Term
| 2 ways epoxides can be formed |
|
Definition
| -the reaction of an alkene with a peroxyacid RCO3H
-when halohydrins are treated with base |
|
|
Term
| 2 ways water can be added to alkenes |
|
Definition
-hydration
-oxymercuration |
|
|
Term
| 3 molecules of ______ add to BH3 to produce a trialkylborane |
|
Definition
|
|
Term
| 3 molecules of alkene add to BH3 to produce ______ |
|
Definition
|
|
Term
| 3 molecules of alkene add to ______ to produce a trialkylborane |
|
Definition
|
|
Term
| As in ______, the more stable radical (more substituted) is formed in preference to the less stable radical |
|
Definition
| electrophilic addition reactions |
|
|
Term
| As in electrophilic addition reactions, the ______ is formed in preference to the less stable radical |
|
Definition
| more stable radical (more substituted) |
|
|
Term
| As in electrophilic addition reactions, the more stable radical (more substituted) is formed in preference to ______ |
|
Definition
|
|
Term
| BH3 adds to ______ to produce an organoborane |
|
Definition
|
|
Term
| BH3 adds to an alkene to produce ______ |
|
Definition
|
|
Term
| Br2 and Cl2 react with ______ to yield 1,2-dihaloalkenes |
|
Definition
|
|
Term
| Br2 and Cl2 react with alkenes to yield ______ |
|
Definition
|
|
Term
| Carbon-halogen bonds are... |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
| lithium diorganocopper compounds (R2CuLi) |
|
|
Term
|
Definition
| organomagnesium halides, RMgX |
|
|
Term
| Grignard reagents can be formed from ______ |
|
Definition
| alkyl, alkenyl, and aryl halides |
|
|
Term
| Grignard reagents react with ______ to form hydrocarbons |
|
Definition
|
|
Term
| Grignard reagents react with weak acids to form ______ |
|
Definition
|
|
Term
| HX and X2 add to alkynes by... |
|
Definition
| an electrophilic addition mechanism |
|
|
Term
| KMnO4 in ______ cleaves alkenes to yield ketones, carboxylic acids, or CO2 |
|
Definition
| neutral or acidic solution |
|
|
Term
| KMnO4 in ______ cleaves alkenes to yield ketones, carboxylic acids, or CO2 |
|
Definition
| neutral or acidic solution |
|
|
Term
| KMnO4 in neutral or acidic solution ______ alkenes to yield ketones, carboxylic acids, or CO2 |
|
Definition
|
|
Term
| KMnO4 in neutral or acidic solution ______ alkenes to yield ketones, carboxylic acids, or CO2 |
|
Definition
|
|
Term
| KMnO4 in neutral or acidic solution cleaves ______ to yield ketones, carboxylic acids, or CO2 |
|
Definition
|
|
Term
| KMnO4 in neutral or acidic solution cleaves ______ to yield ketones, carboxylic acids, or CO2 |
|
Definition
|
|
Term
| KMnO4 in neutral or acidic solution cleaves alkenes to yield ______ |
|
Definition
| ketones, carboxylic acids, or CO2 |
|
|
Term
| KMnO4 in neutral or acidic solution cleaves alkenes to yield ______ |
|
Definition
| ketones, carboxylic acids, or CO2 |
|
|
Term
|
Definition
| when a substituent is added to the more substituted C |
|
|
Term
|
Definition
| when a substituent is added to the more substituted C |
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
| O3 (ozone) causes ______ of an alkene to produce aldehyde and/or ketone fragments |
|
Definition
|
|
Term
| O3 (ozone) causes ______ of an alkene to produce aldehyde and/or ketone fragments |
|
Definition
|
|
Term
| O3 (ozone) causes cleavage of ______ to produce aldehyde and/or ketone fragments |
|
Definition
|
|
Term
| O3 (ozone) causes cleavage of ______ to produce aldehyde and/or ketone fragments |
|
Definition
|
|
Term
| O3 (ozone) causes cleavage of an alkene to produce ______ |
|
Definition
| aldehyde and/or ketone fragments |
|
|
Term
| O3 (ozone) causes cleavage of an alkene to produce ______ |
|
Definition
| aldehyde and/or ketone fragments |
|
|
Term
| O3 (ozone) causing cleavage of an alkene to produce aldehyde and/or ketone fragments proceeds thru... |
|
Definition
| a cyclic molozonide, which rearranges to an ozonide that is reduced by Zn |
|
|
Term
| O3 (ozone) causing cleavage of an alkene to produce aldehyde and/or ketone fragments proceeds thru... |
|
Definition
| a cyclic molozonide, which rearranges to an ozonide that is reduced by Zn |
|
|
Term
| O3 or KMnO4 cleave ______ to produce carboxylic acids or CO2 (terminal alkyne) |
|
Definition
|
|
Term
| O3 or KMnO4 cleave alkyne bonds to produce ______ |
|
Definition
| carboxylic acids or CO2 (terminal alkyne) |
|
|
Term
| OsO4 causes ______ of 2 -OH groups to an alkene to form a diol |
|
Definition
|
|
Term
| OsO4 causes ______ of 2 -OH groups to an alkene to form a diol |
|
Definition
|
|
Term
| OsO4 causes the addition of 2 -OH groups to ______ to form a diol |
|
Definition
|
|
Term
| OsO4 causes the addition of 2 -OH groups to ______ to form a diol |
|
Definition
|
|
Term
| OsO4 causes the addition of 2 -OH groups to an alkene to form a ______ |
|
Definition
|
|
Term
| OsO4 causes the addition of 2 -OH groups to an alkene to form a ______ |
|
Definition
|
|
Term
| OsO4 causes the addition of ______ to an alkene to form a diol |
|
Definition
|
|
Term
| OsO4 causes the addition of ______ to an alkene to form a diol |
|
Definition
|
|
Term
|
Definition
| Pd catalyzed coupling of aryl or vinyl organotin reagents with organohalides |
|
|
Term
| ______ (-NH2) can deprotenate a terminal alkyne, yielding an acetylide anion |
|
Definition
|
|
Term
| ______ (CH2I2, Zn-Cu) produces a non-halogenated cyclopropane via a carbenoid reagent |
|
Definition
| the Simmons-Smith reaction |
|
|
Term
| ______ (R2C:) adds to an alkene to give a cyclopropane |
|
Definition
|
|
Term
| ______ add HO-X (X = Br or Cl), forming halohydrins, when they react with halogens in the presence of H2O |
|
Definition
|
|
Term
| ______ adds to alkenes to yield alcohols in the presence of a strong acid catalyst |
|
Definition
|
|
Term
| ______ adds to an alkene to produce an organoborane |
|
Definition
|
|
Term
| ______ alkyl chlorides, bromides, or iodides can be prepared by the rxn of a tertiary alcohol with HCl, HBr, or HI |
|
Definition
|
|
Term
| ______ are limited to primary alkyl bromides and iodides |
|
Definition
|
|
Term
| ______ can be cleaved with HIO4 (periodic acid) to produce carbonyl compounds |
|
Definition
|
|
Term
| ______ can be cleaved with HIO4 (periodic acid) to produce carbonyl compounds |
|
Definition
|
|
Term
| ______ can be formed by treatment of the corresponding alcohols with SOCl2 or PBr3, respectively |
|
Definition
| primary and secondary alkyl chlorides and bromides |
|
|
Term
| ______ can be formed from alkyl, alkenyl, and aryl halides |
|
Definition
|
|
Term
| ______ can be prepared by the reaction of an alkene with a peroxyacid RCO3H |
|
Definition
|
|
Term
| ______ can be prepared using either (CH3CH2)2 NSF3 or HF in a pyridine |
|
Definition
|
|
Term
| ______ can combine with CuI to form lithium diorganocopper compounds (R2CuLi), which are known as Gilman reagents |
|
Definition
|
|
Term
| ______ can form an alkylation proiduct |
|
Definition
|
|
Term
| ______ can react with Li to form alkyllithiums |
|
Definition
|
|
Term
| ______ can react with alkyl halides (except for fluorides) to form hydrocarbon products |
|
Definition
| lithium diorganocopper compounds (R2CuLi) |
|
|
Term
| ______ can react with haloalkanes to form substitution products |
|
Definition
|
|
Term
| ______ cause dehydrohalogenation rxns with secondary and tertiary halides |
|
Definition
|
|
Term
| ______ causes cleavage of an alkene to produce aldehyde and/or ketone fragments |
|
Definition
|
|
Term
| ______ causes cleavage of an alkene to produce aldehyde and/or ketone fragments |
|
Definition
|
|
Term
| ______ causes the addition of 2 -OH groups to an alkene to form a diol |
|
Definition
|
|
Term
| ______ causes the addition of 2 -OH groups to an alkene to form a diol |
|
Definition
|
|
Term
| ______ cleave alkyne bonds to produce carboxylic acids or CO2 (terminal alkyne) |
|
Definition
|
|
Term
| ______ give alkynes when treated with a strong base |
|
Definition
|
|
Term
| ______ in a bicyclic ring system is endo if it is syn to the larger of the other 2 bridges |
|
Definition
|
|
Term
| ______ in neutral or acidic solution cleaves alkenes to yield ketones, carboxylic acids, or CO2 |
|
Definition
|
|
Term
| ______ in neutral or acidic solution cleaves alkenes to yield ketones, carboxylic acids, or CO2 |
|
Definition
|
|
Term
| ______ is complementary to Hg(II)-catalyzed hydration |
|
Definition
|
|
Term
| ______ is complementary to oxymercuration/reduction |
|
Definition
|
|
Term
| ______ is formed from an epoxycycloalkane |
|
Definition
|
|
Term
| ______ is formed from an epoxycycloalkane |
|
Definition
|
|
Term
| ______ is sensitive to the steric environment around the double bond |
|
Definition
| catalytic hydrogenation of alkenes |
|
|
Term
| ______ is/are at the lowest oxidation level and ______ is/are at the highest level |
|
Definition
|
|
Term
| ______ occurs at the allylic position because an allylic C-H bond is weaker than most other C-H bonds, and the allylic radical is more stable |
|
Definition
| allylic bromination of alkenes |
|
|
Term
| ______ of a terminal alkyne gives an aldehyde |
|
Definition
|
|
Term
| ______ of an epoxide ring with water yields a 1,2-diol (glycol) |
|
Definition
|
|
Term
| ______ of an internal alkyne gives a ketone |
|
Definition
|
|
Term
| ______ of dichlorocarbene to a double bond is stereospecific, and only cis-dichlorocyclopropanes are formed |
|
Definition
|
|
Term
| ______ react in electrophilic addition reactions to give products of both 1,2-addition and 1,4 addition |
|
Definition
|
|
Term
| ______ react with alkenes to yield 1,2-dihaloalkenes |
|
Definition
|
|
Term
| ______ reactions yield a single enantiomer, even when the substrate is achiral |
|
Definition
|
|
Term
| ______ reduces alkenes to saturated hydrocarbons |
|
Definition
|
|
Term
| ______ rxns are useful for forming large molecules from small pieces |
|
Definition
|
|
Term
| a carbene (R2C:) ______ an alkene to give a cyclopropane |
|
Definition
|
|
Term
| a carbene (R2C:) adds to ______ to give a cyclopropane |
|
Definition
|
|
Term
| a carbene (R2C:) adds to an alkene to give ______ |
|
Definition
|
|
Term
| a carbene (______) adds to an alkene to give a cyclopropane |
|
Definition
|
|
Term
| a mixture of products may form at the end of an allylic radical rxn if... |
|
Definition
| the alkene is unsymmetrical |
|
|
Term
| a rxn that converts a compound from a higher oxidation level to a lower oxidation level is... |
|
Definition
|
|
Term
| a rxn that converts a compound from a lower oxidation level to a higher oxidation level is... |
|
Definition
|
|
Term
| a safer version of the hydroxylation of alkenes uses... |
|
Definition
| a catalytic amount of OsO4 and the oxidant NMO |
|
|
Term
| a safer version of the hydroxylation of alkenes uses... |
|
Definition
| a catalytic amount of OsO4 and the oxidant NMO |
|
|
Term
| a substituent in ______ is endo if it is syn to the larger of the other 2 bridges |
|
Definition
|
|
Term
| a substituent in a bicyclic ring system is ______ if it is syn to the larger of the other 2 bridges |
|
Definition
|
|
Term
| a substituent in a bicyclic ring system is endo if... |
|
Definition
| it is syn to the larger of the other 2 bridges |
|
|
Term
| a trans-1,2-diol is formed from ______ |
|
Definition
|
|
Term
| a trans-1,2-diol is formed from ______ |
|
Definition
|
|
Term
| acetylide alkylations are limited to... |
|
Definition
| primary alkyl bromides and iodides |
|
|
Term
| acetylide anions are stabilized by... |
|
Definition
| the large amount of "s character" of the orbital that holds the electron |
|
|
Term
| acetylide anions are strongly (electrophilic or nucleophilic) |
|
Definition
|
|
Term
| acetylide anions can react with ______ to form substitution products |
|
Definition
|
|
Term
| acetylide anions can react with haloalkanes to form ______ |
|
Definition
|
|
Term
| acetylide ions cause ______ with secondary and tertiary halides |
|
Definition
|
|
Term
| acetylide ions cause dehydrohalogenation rxns with ______ |
|
Definition
| secondary and tertiary halides |
|
|
Term
| acid-catalyzed rxn of ______ with water yields a 1,2-diol (glycol) |
|
Definition
|
|
Term
| acid-catalyzed rxn of an epoxide ring with ______ yields a 1,2-diol (glycol) |
|
Definition
|
|
Term
| acid-catalyzed rxn of an epoxide ring with water yields a ______ |
|
Definition
|
|
Term
| acid-catalyzed rxn of an epoxide ring with water yields a ______ |
|
Definition
|
|
Term
| acidity of terminal alkynes |
|
Definition
|
|
Term
| addition of ______ to a double bond is stereospecific, and only cis-dichlorocyclopropanes are formed |
|
Definition
|
|
Term
| addition of dichlorocarbene to ______ is stereospecific, and only cis-dichlorocyclopropanes are formed |
|
Definition
|
|
Term
| addition of dichlorocarbene to a double bond is ______, and only cis-dichlorocyclopropanes are formed |
|
Definition
|
|
Term
| addition of dichlorocarbene to a double bond is stereospecific, and only ______ are formed |
|
Definition
| cis-dichlorocyclopropanes |
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
| alkenes add HO-X (X = Br or Cl), forming ______, when they react with halogens in the presence of H2O |
|
Definition
|
|
Term
| alkenes add HO-X (X = Br or Cl), forming halohydrins, when they react with ______ in the presence of H2O |
|
Definition
|
|
Term
| alkenes add HO-X (X = Br or Cl), forming halohydrins, when they react with halogens in the presence of ______ |
|
Definition
|
|
Term
| alkenes add ______, forming halohydrins, when they react with halogens in the presence of H2O |
|
Definition
|
|
Term
| alkyl fluorides can be prepared using either (CH3CH2)2 NSF3 or HF in a ______ |
|
Definition
|
|
Term
| alkyl fluorides can be prepared using either ______ or ______ in a pyridine |
|
Definition
|
|
Term
| alkyl halides behave as ______ in polar rxns |
|
Definition
|
|
Term
| alkyl halides behave as electrophiles in ______ rxns |
|
Definition
|
|
Term
| alkyl halides can react with Li to form ______ |
|
Definition
|
|
Term
| alkyl halides can react with ______ to form alkyllithiums |
|
Definition
|
|
Term
|
Definition
| nucleophilic acetylide anion attacking the electrophilic C of the haloalkene |
|
|
Term
| alkyllithiums can combine with CuI to form ______, which are known as Gilman reagents |
|
Definition
| lithium diorganocopper compounds (R2CuLi) |
|
|
Term
| alkyllithiums can combine with CuI to form lithium diorganocopper compounds (R2CuLi), which are known as ______ |
|
Definition
|
|
Term
| alkyllithiums can combine with ______ to form lithium diorganocopper compounds (R2CuLi), which are known as Gilman reagents |
|
Definition
|
|
Term
| alkyne triple bonds result from... |
|
Definition
| the overlap of 2 sp-hybridized C atoms |
|
|
Term
| alkynes are somewhat (more or less) reactive than alkenes in electrophilic addition rxns |
|
Definition
|
|
Term
| alkynes are somewhat less reactive than alkenes in ______ rxns |
|
Definition
|
|
Term
| alkynes can be prepared by ______ rxns of 1,2-dihalides, using strong base |
|
Definition
|
|
Term
| alkynes can be prepared by elimination rxns of 1,2-dihalides, using ______ |
|
Definition
|
|
Term
| alkynes can be prepared by elimination rxns of ______, using strong base |
|
Definition
|
|
Term
|
Definition
| C's adjacent to an alkene |
|
|
Term
| allylic bromination of alkenes occurs at ______ because an allylic C-H bond is weaker than most other C-H bonds, and the allylic radical is more stable |
|
Definition
|
|
Term
| allylic bromination of alkenes occurs at the allylic position because... |
|
Definition
| an allylic C-H bond is weaker than most other C-H bonds, and the allylic radical is more stable |
|
|
Term
| although hydration of alkenes is important industrially,... |
|
Definition
| reaction conditions are too severe for most molecules |
|
|
Term
| anions typically form under (acidic or basic) conditions |
|
Definition
|
|
Term
|
Definition
| addition of 2 substituents from opposite sides of the plane |
|
|
Term
|
Definition
| addition of 2 substituents from opposite sides of the plane |
|
|
Term
| anti-Markovnikov addition |
|
Definition
| when a substituent is added to the less substituted C |
|
|
Term
| anti-Markovnikov addition |
|
Definition
| when a substituent is added to the less substituted C |
|
|
Term
|
Definition
| C's adjacent to a phenyl group |
|
|
Term
| biochemical radical reactions are (more or less) controlled than laboratory radical reactions |
|
Definition
|
|
Term
| bond length in alkyl halides vs. size of halogen bonded to the C |
|
Definition
directly proportional
bond lengths increase with increasing size of the halogen |
|
|
Term
| bond strength in alkyl halides vs. size of halogen bonded to the C |
|
Definition
inversely proportional
bond strengths decrease with increasing size of the halogen |
|
|
Term
|
Definition
|
|
Term
| catalytic hydrogenation ______ alkenes to saturated hydrocarbons |
|
Definition
|
|
Term
| catalytic hydrogenation is a ______ process that takes place on the surface of the catalyst |
|
Definition
|
|
Term
| catalytic hydrogenation is a heterogeneous process that takes place ______ |
|
Definition
| on the surface of the catalyst |
|
|
Term
| catalytic hydrogenation of alkenes is sensitive to ______ around the double bond |
|
Definition
|
|
Term
| catalytic hydrogenation of alkenes is sensitive to the steric environment around ______ |
|
Definition
|
|
Term
| catalytic hydrogenation reduces ______ to saturated hydrocarbons |
|
Definition
|
|
Term
| catalytic hydrogenation reduces alkenes to ______ |
|
Definition
|
|
Term
| cations typically form under (acidic or basic) conditions |
|
Definition
|
|
Term
| complete reduction of an alkyne to an alkane occurs when... |
|
Definition
|
|
Term
| conjugated dienes react in ______ reactions to give products of both 1,2-addition and 1,4 addition |
|
Definition
|
|
Term
| conjugated dienes react in electrophilic addition reactions to give products of ______ |
|
Definition
| both 1,2-addition and 1,4 addition |
|
|
Term
|
Definition
|
|
Term
|
Definition
| treatment of an alcohol with a strong base forms an alkene, with loss of H2O |
|
|
Term
|
Definition
| rxn of an alkyl halide with a strong base forms an alkene, with loss of HX |
|
|
Term
|
Definition
| losing halogen at 1 site and losing H at another site |
|
|
Term
| depiction of cleavage of 1,2-diols |
|
Definition
|
|
Term
| depiction of dichlorocarbene addition |
|
Definition
|
|
Term
| depiction of oxidative cleavage of alkenes by ozonolysis |
|
Definition
|
|
Term
| depiction of oxidative cleavage of alkenes by rxn of KMnO4 in acidic solution |
|
Definition
|
|
Term
| depiction of the Diels-Alder mechanism |
|
Definition
|
|
Term
| depiction of the Simmons-Smith rxn |
|
Definition
|
|
Term
|
Definition
| alkene that seeks out diene |
|
|
Term
| diols can be ______ with HIO4 (periodic acid) to produce carbonyl compounds |
|
Definition
|
|
Term
| diols can be ______ with HIO4 (periodic acid) to produce carbonyl compounds |
|
Definition
|
|
Term
| diols can be cleaved with HIO4 (periodic acid) to produce ______ |
|
Definition
|
|
Term
| diols can be cleaved with HIO4 (periodic acid) to produce ______ |
|
Definition
|
|
Term
| diols can be cleaved with ______ to produce carbonyl compounds |
|
Definition
|
|
Term
| diols can be cleaved with ______ to produce carbonyl compounds |
|
Definition
|
|
Term
| elimination rxns generally form... |
|
Definition
|
|
Term
|
Definition
[image]
alkene and alcohol |
|
|
Term
|
Definition
| compounds with 2bl bonds and triple bonds |
|
|
Term
| enzyme-catalyzed reactions yield ______, even when the substrate is achiral |
|
Definition
|
|
Term
| enzyme-catalyzed reactions yield a single enantiomer, even when the substrate is ______ |
|
Definition
|
|
Term
| epoixides can be formed when ______ are treated with base |
|
Definition
|
|
Term
| epoixides can be formed when halohydrins are treated with ______ |
|
Definition
|
|
Term
|
Definition
| a 3-membered-ring functional group |
|
|
Term
|
Definition
|
|
Term
| epoxides can be prepared by the reaction of ______ with a peroxyacid RCO3H |
|
Definition
|
|
Term
| epoxides can be prepared by the reaction of an alkene with ______ |
|
Definition
|
|
Term
| epoxides can be prepared by... |
|
Definition
| -the reaction of an alkene with a peroxyacid RCO3H
-when halohydrins are treated with base |
|
|
Term
| example of how deuterium is incorporated into the nomenclature of a molecule |
|
Definition
| 2-deutero-1-methylcyclopentene |
|
|
Term
| examples of a rxn using the Diels-Alder process |
|
Definition
|
|
Term
| examples of oxidation of a C include ______ and reduction of alkenes with Br2 |
|
Definition
|
|
Term
| examples of oxidation of a C include chloronation of alkanes and ______ |
|
Definition
| reduction of alkenes with Br2 |
|
|
Term
| examples of reduction of a C include ______, and reduction of an alkene with H2 |
|
Definition
| conversion of a Grignard reagent to an alkene |
|
|
Term
| examples of reduction of a C include conversion of a Grignard reagent to an alkene, and ______ |
|
Definition
| reduction of an alkene with H2 |
|
|
Term
| general depiction of an alkyne |
|
Definition
|
|
Term
| geometry of alkyl halides |
|
Definition
|
|
Term
|
Definition
| addition of halogens to alkenes |
|
|
Term
|
Definition
| a 1,2-haloalcohol, such as that obtained on addition of HOBr to an alkene |
|
|
Term
| halohydrin formation to alkenes |
|
Definition
| reacting alkenes with X2 and H2O |
|
|
Term
| how HX and X2 add to alkynes by an electrophilic addition mechanism |
|
Definition
-addition of 2 equivalents of HX occurs if the acid is in excess
-addition occurs with Makovnikov regiochemistry and trans stereochemistry |
|
|
Term
| how a cyclic halonium intermediate is formed |
|
Definition
| in a single step by an interaction of an alkene with Br+ or Cl+ |
|
|
Term
| how bromohydrins are formed when hypophalous acids are added to alkenes |
|
Definition
| bromohydrin formation is usually achieved by NBS in aqueous DMSO |
|
|
Term
| how halohydrins are formed when hypohalous acids are added to alkenes |
|
Definition
| the added nucleophile (H2O) intercepts the halonium ion to yield a halohydrin |
|
|
Term
| how hydroxylation of alkenes occurs |
|
Definition
| OsO4 causes the addition of 2 -OH groups to an alkene to form a diol |
|
|
Term
| how hydroxylation of alkenes occurs |
|
Definition
| OsO4 causes the addition of 2 -OH groups to an alkene to form a diol |
|
|
Term
| how many times does the propagation phase of the chain-growth polymerization reaction occur? |
|
Definition
| this step is repeated many, many times |
|
|
Term
| how molecular orbital theory offers an explanation for the stability of 1,3-butadiene |
|
Definition
-if we combine 4 adjacent p orbitals, we generate a set of 4 molecular orbitals
-bonding electrons go into the lower molecular orbitals
-the lowest molecular orbital has a bonding interaction between C2 and C3 that gives that bond partial 2bl-bond character
-the pi electrons of butadiene are delocalized over this entire pi framework |
|
|
Term
| how ozone develops in the air |
|
Definition
|
|
Term
| how ozone reacts with alkenes |
|
Definition
| breaks that double bond to yield 2 products that contain a 2bl bond with on O at the end |
|
|
Term
| how reduction occurs in organic chemistry |
|
Definition
| either by forming C-H bonds or by breaking C-O, C-N, or C-X bonds |
|
|
Term
| how resonance stabilizes allylic radicals |
|
Definition
| because the unpaired electron is spread out over an extended pi network |
|
|
Term
| how ring-opening of an epoxide ring occurs in an acid-catalyzed reaction of an epoxide ring with water |
|
Definition
| by back-side attack of a nucleophile on the protenated epoxide ring |
|
|
Term
| how ring-opening of an epoxide ring occurs in an acid-catalyzed reaction of an epoxide ring with water |
|
Definition
| by back-side attack of a nucleophile on the protenated epoxide ring |
|
|
Term
| how the C2-C3 bond in 1,3-butadiene obtains partial 2bl bond character |
|
Definition
| the lowest MO has a bonding interaction between C2 and C3 that gives that bond partial 2bl-bond character |
|
|
Term
| how the Diels-Alder cycloaddition rxn occurs |
|
Definition
| -a diene can react with certain alkenes to form a cyclic product
-this rxn forms 2 new C-C bonds in a single step
-the rxn occurs by a pericyclic mechanism, which takes place in a step by a cyclic redistribution of electrons
-in the rxn, sigma overlap occurs between the 2 alkene p orbitals and the 2 p orbitals on C's 1 and 4 of the diene
-the 2 alkene C's and C1 and C4 of the diene rehybridize from sp2 to sp3, and C2 and C3 of the diene remain sp2 hybridized |
|
|
Term
| how the addition of carbenes to alkenes occurs |
|
Definition
| in a single step, without intermediates |
|
|
Term
| how the radical chain mechanism occurs in allylic bromination of alkenes |
|
Definition
| 1: Br• abstracts an allylic H
2: the allylic radical reacts with Br2 to form an allylic bromide, plus Br• |
|
|
Term
| how the reaction of an alkene with a peroxyacid RCO3H to form an epoxide occurs |
|
Definition
| occurs in 1 step with syn stereochemistry |
|
|
Term
|
Definition
| Keq = ([product 1][product 2]...[product x])/([reactant 1][reactant 2]...[reactant x]) |
|
|
Term
| how to calculate change in energy (ΔG) |
|
Definition
ΔG = ΔH - TΔS
ΔG = change in energy
ΔH = change in enthalpy
T = temp in K
ΔS = change in entropy |
|
|
Term
| how to calculate the rate of a rxn |
|
Definition
| rate = k[reactant 1][reactant 2]...[reactant x] |
|
|
Term
| how vulcanization hardens rubber |
|
Definition
| heating it with S forms cross links that lock the chains together |
|
|
Term
| how we know conjugated dienes are more stable than nonconjugated dienes |
|
Definition
| lower heat of hydrogenation, which means they release less heat on hydrogenation |
|
|
Term
|
Definition
| addition of 2 -OH groups to a 2bl bond |
|
|
Term
|
Definition
| addition of 2 -OH groups to a 2bl bond |
|
|
Term
|
Definition
| addition of water to a molecule, such as occurs when alkenes are treated with aqueous to give alcohols |
|
|
Term
|
Definition
| addition of borane (BH3) or an alkylborane to an alkene. The resultant trialkylborane products can be oxidized to yield alcohols. |
|
|
Term
| hydroboration /oxidation of alkynes gives an intermediate ______ product that tautomerizes to a carbonyl product |
|
Definition
|
|
Term
| hydroboration /oxidation of alkynes gives an intermediate enol product that ______ to a carbonyl product |
|
Definition
|
|
Term
| hydroboration /oxidation of alkynes gives an intermediate enol product that tautomerizes to ______ product |
|
Definition
|
|
Term
| hydroboration is ______ to oxymercuration/reduction |
|
Definition
|
|
Term
| hydroboration is complementary to ______ |
|
Definition
|
|
Term
| hydroboration of ______ gives a ketone |
|
Definition
|
|
Term
| hydroboration of ______ gives an aldehyde |
|
Definition
|
|
Term
| hydroboration of a terminal alkyne gives ______ |
|
Definition
|
|
Term
| hydroboration of an internal alkyne gives ______ |
|
Definition
|
|
Term
| hydroboration/oxidation is ______ to Hg(II)-catalyzed hydration |
|
Definition
|
|
Term
| hydroboration/oxidation is complementary to ______ |
|
Definition
| Hg(II)-catalyzed hydration |
|
|
Term
| hydroxylation of alkenes occurs thru... |
|
Definition
|
|
Term
| hydroxylation of alkenes occurs thru... |
|
Definition
|
|
Term
| if more than 1 type of H is present during the radical halogenation of an alkane,... |
|
Definition
| more than 1 type of monosubstituted product is formed |
|
|
Term
| if more than 1 type of ______ is present during the radical halogenation of an alkane, more than 1 type of monosubstituted product is formed |
|
Definition
|
|
Term
| if we combine 4 adjacent p orbitals, we generate... |
|
Definition
| a set of 4 molecular orbitals |
|
|
Term
| in Grignard reagents, the C bonded to Mg is ______ and is nucleophilic |
|
Definition
|
|
Term
| in Grignard reagents, the C bonded to Mg is negatively polarized and is ______ |
|
Definition
|
|
Term
| in Grignard reagents, the C bonded to ______ is negatively polarized and is nucleophilic |
|
Definition
|
|
Term
| in Grignard reagents, the ______ bonded to Mg is negatively polarized and is nucleophilic |
|
Definition
|
|
Term
| in Hg(II)-catalyzed additions of ______, the -OH group adds to the more substituted C to give Markovnikov product |
|
Definition
|
|
Term
| in Hg(II)-catalyzed additions of alkynes, the -OH group adds to ______ to give Markovnikov product |
|
Definition
|
|
Term
| in Hg(II)-catalyzed additions of alkynes, the -OH group adds to the more substituted C to give ______ |
|
Definition
|
|
Term
| in Hg(II)-catalyzed additions of alkynes, the ______ adds to the more substituted C to give Markovnikov product |
|
Definition
|
|
Term
| in Hg(II)-catalyzed additions of alkynes, the intermediate ______ product tautomerizes to a ketone |
|
Definition
|
|
Term
| in Hg(II)-catalyzed additions of alkynes, the intermediate enol product ______ to a ketone |
|
Definition
|
|
Term
| in Hg(II)-catalyzed additions of alkynes, the intermediate enol product tautomerizes to ______ |
|
Definition
|
|
Term
| in ______, addition of Hg(OAc)2, followed by NaBH4, converts an alkene to an alcohol |
|
Definition
|
|
Term
| in ______, the mechanism of addition proceeds through a mercurinium ion |
|
Definition
|
|
Term
| in ______, the nucleophilic acetylide anion attacks the electrophilic C of haloalkane to produce a new alkyne |
|
Definition
|
|
Term
| in an alkylation rxn, the ______ attacks the electrophilic C of haloalkane to produce a new alkyne |
|
Definition
| nucleophilic acetylide anion |
|
|
Term
| in an alkylation rxn, the nucleophilic acetylide anion attacks the ______ to produce a new alkyne |
|
Definition
| electrophilic C of haloalkane |
|
|
Term
| in an alkylation rxn, the nucleophilic acetylide anion attacks the electrophilic C of haloalkane to produce ______ |
|
Definition
|
|
Term
| in an allylic radical, the C with the unpaired electron is ______, and its p orbital can overlap with the p orbitals of the 2bl bond C's |
|
Definition
|
|
Term
| in an allylic radical, the C with the unpaired electron is sp2 hybridized, and its ______ can overlap with the p orbitals of the 2bl bond C's |
|
Definition
|
|
Term
| in an allylic radical, the C with the unpaired electron is sp2 hybridized, and its p orbital can overlap with ______ |
|
Definition
| the p orbitals of the 2bl bond C's |
|
|
Term
| in an allylic radical, the ______ is sp2 hybridized, and its p orbital can overlap with the p orbitals of the 2bl bond C's |
|
Definition
| C with the unpaired electron |
|
|
Term
| in electrophilic addition of conjugated dienes, addition of ______ gives an allylic carbocation intermediate that is resonance-stabilized |
|
Definition
|
|
Term
| in electrophilic addition of conjugated dienes, addition of an electrophile gives ______ carbocation intermediate that is resonance-stabilized |
|
Definition
|
|
Term
| in electrophilic addition of conjugated dienes, addition of an electrophile gives an allylic ______ that is resonance-stabilized |
|
Definition
|
|
Term
| in electrophilic addition of conjugated dienes, addition of an electrophile gives an allylic carbocation intermediate that is ______ |
|
Definition
|
|
Term
| in electrophilic addition of conjugated dienes, addition of the ______ in the 2nd step of the rxn can occur at either end of the carbocation to yield 2 products |
|
Definition
|
|
Term
| in electrophilic addition of conjugated dienes, addition of the nucleophile in the 2nd step of the rxn can occur at ______ end of the carbocation to yield 2 products |
|
Definition
|
|
Term
| in electrophilic addition of conjugated dienes, addition of the nucleophile in the 2nd step of the rxn can occur at either end of the ______ to yield 2 products |
|
Definition
|
|
Term
| in electrophilic addition of conjugated dienes, addition of the nucleophile in the 2nd step of the rxn can occur at either end of the carbocation to yield ______ |
|
Definition
|
|
Term
| in electrophilic addition of conjugated dienes, addition of the nucleophile in the ______ step of the rxn can occur at either end of the carbocation to yield 2 products |
|
Definition
|
|
Term
| in electrophilic addition rxns of conjugated dienes, is the 1,2 adduct kinetic or thermodynamic? |
|
Definition
|
|
Term
| in electrophilic addition rxns of conjugated dienes, is the 1,4 adduct kinetic or thermodynamic? |
|
Definition
|
|
Term
| in electrophilic addition rxns of conjugated dienes, which product preferentially forms at low high? |
|
Definition
|
|
Term
| in electrophilic addition rxns of conjugated dienes, which product preferentially forms at low temp? |
|
Definition
|
|
Term
| in organic chemistry, oxidation decreases how ocidation occurs in organic chemistry |
|
Definition
| either by forming C-O, C-N, or C-X bonds or by breaking C-H bonds |
|
|
Term
| in oxymercuration, addition of Hg(OAc)2, followed by NaBH4, converts ______ to an alcohol |
|
Definition
|
|
Term
| in oxymercuration, addition of Hg(OAc)2, followed by NaBH4, converts an alkene to ______ |
|
Definition
|
|
Term
| in oxymercuration, addition of Hg(OAc)2, followed by ______, converts an alkene to an alcohol |
|
Definition
|
|
Term
| in oxymercuration, addition of ______, followed by NaBH4, converts an alkene to an alcohol |
|
Definition
|
|
Term
| in oxymercuration, the mechanism of ______ proceeds through a mercurinium ion |
|
Definition
|
|
Term
| in oxymercuration, the mechanism of addition proceeds through a ______ |
|
Definition
|
|
Term
| in retrosynthesis, what happens to 2bl bonded O's that are neither ketones nor aldehydes? |
|
Definition
|
|
Term
| in the Diels-Alder cycloaddition rxn, ______ can react with certain alkenes to form a cyclic product |
|
Definition
|
|
Term
| in the Diels-Alder cycloaddition rxn, a diene can react with ______ to form a cyclic product |
|
Definition
|
|
Term
| in the Diels-Alder cycloaddition rxn, a diene can react with certain alkenes to form ______ |
|
Definition
|
|
Term
| in the Diels-Alder rxn, ______ occurs between the 2 alkene p orbitals and the 2 p orbitals on C's 1 and 4 of the diene |
|
Definition
|
|
Term
| in the Diels-Alder rxn, sigma overlap occurs between the 2 alkene p orbitals and the 2 p orbitals on ______ |
|
Definition
|
|
Term
| in the Diels-Alder rxn, sigma overlap occurs between the 2 alkene p orbitals and the ______ on C's 1 and 4 of the diene |
|
Definition
|
|
Term
| in the Diels-Alder rxn, sigma overlap occurs between the ______ and the 2 p orbitals on C's 1 and 4 of the diene |
|
Definition
|
|
Term
| in the Diels-Alder rxn, the 2 alkene C's and C1 and C4 of the diene rehybridize from ______ to ______, and C2 and C3 of the diene remain sp2 hybridized |
|
Definition
|
|
Term
| in the Diels-Alder rxn, the 2 alkene C's and C1 and C4 of the diene rehybridize from sp2 to sp3, and C2 and C3 of the diene remain ______ |
|
Definition
|
|
Term
| in the Diels-Alder rxn, the 2 alkene C's and C1 and C4 of the diene rehybridize from sp2 to sp3, and ______ remain sp2 hybridized |
|
Definition
|
|
Term
| in the Diels-Alder rxn, the ______ must have an electron-withdrawing group and may contain a triple bond |
|
Definition
|
|
Term
| in the Diels-Alder rxn, the ______ rehybridize from sp2 to sp3, and C2 and C3 of the diene remain sp2 hybridized |
|
Definition
| 2 alkene C's and C1 and C4 of the diene |
|
|
Term
| in the Diels-Alder rxn, the dienophile must have ______ and may contain a triple bond |
|
Definition
| an electron-withdrawing group |
|
|
Term
| in the Diels-Alder rxn, the dienophile must have an electron-withdrawing group and may contain ______ |
|
Definition
|
|
Term
| in the Diels=Alder rxn, the ______ of the dienophile is maintained during the reaxtion |
|
Definition
|
|
Term
| in the Diels=Alder rxn, the stereochemistry of the ______ is maintained during the reaxtion |
|
Definition
|
|
Term
| initiation of a chain-growth polymerization reaction |
|
Definition
| involves clevage of a weak bond to form a radical |
|
|
Term
| is breaking of ring strain endothermic or exothermic? |
|
Definition
|
|
Term
| is steric hinderance a barrier to the formation of Grignard reagents? |
|
Definition
|
|
Term
| is the original chirality center affected by the addition of water to a chiral alkene? |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
| kinetic conditions for a rxn |
|
Definition
|
|
Term
|
Definition
| the product in a reaction that forms faster |
|
|
Term
| lithium diorganocopper compounds (R2CuLi) can react with ______ (except for fluorides) to form hydrocarbon products |
|
Definition
|
|
Term
| lithium diorganocopper compounds (R2CuLi) can react with alkyl halides (except for ______) to form hydrocarbon products |
|
Definition
|
|
Term
| lithium diorganocopper compounds (R2CuLi) can react with alkyl halides (except for fluorides) to form ______ |
|
Definition
|
|
Term
| many halomethanes have... |
|
Definition
|
|
Term
| mechanisms of radical reactions are shown using... |
|
Definition
|
|
Term
| opening of epoxides yields (syn or anti) products |
|
Definition
|
|
Term
| organohalides react with Mg to produce... |
|
Definition
| organimagnesium halides (RMgX) |
|
|
Term
| organometallic coupling rxns are useful for ______ |
|
Definition
| forming large molecules from small pieces |
|
|
Term
| organometallic coupling rxns can be carried out on... |
|
Definition
| alkyl, vinyl, and aryl halides |
|
|
Term
|
Definition
| rxn that causes a decrease in electron ownership by C, either by bond formation between C or a more electronegative atom (usually O, N, or a halogen) or by bond breaking between C and a less electronegative atom (usually H) |
|
|
Term
|
Definition
| gain or O or other eneg element or loss of H |
|
|
Term
|
Definition
| a rxn that results in a loss of electron density by a C |
|
|
Term
| oxidation of a C may be due to... |
|
Definition
-bond formation between C and more eneg atom (usually O, N, or halogen)
-bond breaking between C and less eneg atom (usually H) |
|
|
Term
| oxidative cleavage rxns were formerly used for... |
|
Definition
|
|
Term
|
Definition
| a method for double bond hydration by reaction of an alkene with aqueous mercuric acetate followed by treatment with NaBH4 |
|
|
Term
|
Definition
|
|
Term
|
Definition
| breaking of molecule using ozone |
|
|
Term
| partial reduction of an alkyne proceeds through ______ --> vynilic radical --> vinylic anion |
|
Definition
|
|
Term
| partial reduction of an alkyne proceeds through an anion radical --> ______ --> vinylic anion |
|
Definition
|
|
Term
| partial reduction of an alkyne proceeds through an anion radical --> vynilic radical --> ______ |
|
Definition
|
|
Term
| partial reduction of an alkyne to ______ occurs with H2 and a Lindlar catalyst |
|
Definition
|
|
Term
| partial reduction of an alkyne to a cis alkene occurs with ______ and ______ |
|
Definition
|
|
Term
| partial reduction of an alkyne with Li in NH3 produces ______ |
|
Definition
|
|
Term
| partial reduction of an alkyne with ______ in ______ produces a trans alkene |
|
Definition
|
|
Term
|
Definition
| catalyst that has had something put on it to make it less active |
|
|
Term
| polarizability basically means... |
|
Definition
| it can have induced dipole |
|
|
Term
| polymerization of dienes can be initiated by... |
|
Definition
| either a radical or an acid |
|
|
Term
| polymerization of dienes occurs by... |
|
Definition
|
|
Term
| primary and secondary alkyl chlorides and bromides can be formed by ______ with SOCl2 or PBr3, respectively |
|
Definition
| treatment of the corresponding alcohols |
|
|
Term
| primary and secondary alkyl chlorides and bromides can be formed by treatment of the corresponding alcohols with ______ |
|
Definition
| SOCl2 or PBr3, respectively |
|
|
Term
| products of allylic bromination reactions can be ______ to form dienes |
|
Definition
|
|
Term
| products of allylic bromination reactions can be dehydrohalogenated to form ______ |
|
Definition
|
|
Term
| propagation of a chain-growth polymerization reaction |
|
Definition
| the alkyl radical adds to another alkene molecule to yield a second radical |
|
|
Term
| radical halogenation of alkanes continues to produce... |
|
Definition
| di- and polysubstituted products |
|
|
Term
| reaction of ______ alcohols occurs under more drastic conditions, which may destroy other acid-sensitive functional groups |
|
Definition
|
|
Term
| reaction of ______ with the carbocation doesn't occur with equal probability from either side, and the resulting product is an optically active mixture of diastereomeric alcohols |
|
Definition
|
|
Term
| reaction of secondary or primary alcohols occurs under ______, which may destroy other acid-sensitive functional groups |
|
Definition
|
|
Term
| reaction of secondary or primary alcohols occurs under more drastic conditions, which may... |
|
Definition
| destroy other acid-sensitive functional groups |
|
|
Term
| reaction of water with ______ doesn't occur with equal probability from either side, and the resulting product is an optically active mixture of diastereomeric alcohols |
|
Definition
|
|
Term
| reaction of water with the carbocation (does or doesn't) occur with equal probability from either side, and the resulting product is an optically active mixture of diastereomeric alcohols |
|
Definition
|
|
Term
| reaction of water with the carbocation doesn't occur with equal probability from either side, and the resulting product is ______ |
|
Definition
| an optically active mixture of diastereomeric alcohols |
|
|
Term
| reactivity of alkenes vs. reactivity of other functional groups |
|
Definition
| alkenes are much more reactive than other functional groups |
|
|
Term
| reactivity of aromatic rings to halohydrin reagents |
|
Definition
| aromatic rings are inert to halohydrin reagents |
|
|
Term
| reactivity of benzylic and allylic C's |
|
Definition
| tend to be more reactive than non-benzyllic and non-allylic |
|
|
Term
| reactivity of dienes with fixed s-cis geometry |
|
Definition
|
|
Term
| reasons for stability of an allylic radical |
|
Definition
| -the C with the unpaired electron is sp2 hybridized, and its p orbital can overlap with the p orbitals of the 2bl bond C's
-the radical intermediate is thus stabilized by resonance
+the stability is due to delocalization (spreading out) of the unpaired electron over an extended pi network
-reaction of the allylic radical with Br2 can occur at either end of the pi orbital system
+a mixture of products may be formed if the alkene is unsymmetrical
+these products aren's usually formed in equal quantities: rxn to form the more substituted 2bl bond is favored
-products of allylic bromination can be dehydrohalogenated to form dienes |
|
|
Term
|
Definition
| loss of O or another eneg element or gain or H |
|
|
Term
|
Definition
| rxn that results in a gain of electron density by a C |
|
|
Term
| reduction of a C may be due to... |
|
Definition
-bond formation between C and less eneg atom
-bond breaking between C and more eneg atom |
|
|
Term
| regiochemistry and stereochemistry of adding HX to alkenes |
|
Definition
|
|
Term
| regiochemistry and stereochemistry of adding X2 to alkenes |
|
Definition
|
|
Term
| regiochemistry and stereochemistry of addition of carbenes to alkenes to yield cyclopropanes |
|
Definition
|
|
Term
| regiochemistry and stereochemistry of catalytic hydrogenation to alkenes |
|
Definition
no regiochemistry
syn addition |
|
|
Term
| regiochemistry and stereochemistry of epoxidation of alkenes with a peroxyacid |
|
Definition
no regiochemistry
syn addition |
|
|
Term
| regiochemistry and stereochemistry of halohydrin formation to alkenes |
|
Definition
|
|
Term
| regiochemistry and stereochemistry of hydroboration-oxidation to alkenes |
|
Definition
|
|
Term
| regiochemistry and stereochemistry of hydrocylation of alkenes with OsO4 |
|
Definition
no regiochemistry
syn addition |
|
|
Term
| regiochemistry and stereochemistry of oxymercurtation-demercuration to alkenes |
|
Definition
|
|
Term
| regiochemistry and stereochemistry of product of hydroxylation by acid-catalyzed epoxide hydrolysis |
|
Definition
no regiochemistry
anti stereochemistry |
|
|
Term
| regiochemistry with which hydroboration of alkenes occurs |
|
Definition
|
|
Term
| regiochemistry with which oxidation of alkenes occurs |
|
Definition
|
|
Term
| relationship between temp and ΔG |
|
Definition
| increasing temp causes ΔG to become less negative, thus rxn less spontaneous |
|
|
Term
| rubber's ability to stretch and contract is due to... |
|
Definition
| the irregular shapes of the polymer chains |
|
|
Term
| rules for naming alkyl halides |
|
Definition
1: find the longest chain and name it as the parent
+if a 2bl or triple bond is present, the parent chain must contain it
2: number the C atoms of the parent chain, starting at the end nearer the first substituent, whether alkyl or halo
3: number each substituent
+if more than 1 of the same kind of substituent is present, number each, and use the prefixes di-, tri-, tetra-, and so on
+if different halogens are present, number all and list them in alphabetical order
4: if the parent chain can be numbered from either end, start at the end nearer the substituent that has alphabetical priority |
|
|
Term
| rxn of ______ with NBS causes bromination at the position allylic to the 2bl bond |
|
Definition
|
|
Term
| rxn of ______ with a strong base forms an alkene, with loss of HX |
|
Definition
|
|
Term
| rxn of ______ with an achiral reactant leads to unequal amounts of diastereomeric products |
|
Definition
|
|
Term
| rxn of a chiral reactant with ______ leads to unequal amounts of diastereomeric products |
|
Definition
|
|
Term
| rxn of a chiral reactant with an achiral reactant leads to (equal or unequal) amounts of diastereomeric products |
|
Definition
|
|
Term
| rxn of a chiral reactant with an achiral reactant leads to unequal amounts of ______ |
|
Definition
|
|
Term
| rxn of an alkene with NBS causes ______ |
|
Definition
| bromination at the position allylic to the 2bl bond |
|
|
Term
| rxn of an alkene with ______ causes bromination at the position allylic to the 2bl bond |
|
Definition
|
|
Term
| rxn of an alkyl halide with ______ forms an alkene, with loss of HX |
|
Definition
|
|
Term
| rxn of an alkyl halide with a strong base forms ______, with loss of ______ |
|
Definition
|
|
Term
| rxn of the allylic radical with Br2 can occur at... |
|
Definition
| either end of the pi orbital system |
|
|
Term
| since enols aren't very stable, they tend to turn into... |
|
Definition
|
|
Term
| some addition rxns of alkenes |
|
Definition
-halogenation
-addition of hypohalous acids
-addition of water to alkenes
-addition of water to alkenes: hydroboration/oxidation |
|
|
Term
| some alkyl halides are named by first citing the ______ and then citing the ______ |
|
Definition
name of the alkyl group
halogen |
|
|
Term
| some metals that are often used to catalyze rxns where alkenes gain H's |
|
Definition
|
|
Term
| some types of hydration rxns of alkynes |
|
Definition
-Hg(II)-catalyzed additions
-hydroboration/oxidation of alkenes |
|
|
Term
| some types of strain in 3 membered rings |
|
Definition
-angle strain
-torsional strain |
|
|
Term
| some ways alkenes can become oxidized |
|
Definition
-epoxidation
-hydroxylation
-cleavage to carbonyl compounds |
|
|
Term
| some ways alkenes can become oxidized |
|
Definition
-epoxidation
-hydroxylation
-cleavage to carbonyl compounds |
|
|
Term
| some ways alkenes can become reduced |
|
Definition
|
|
Term
| some ways alkenes can become reduced |
|
Definition
|
|
Term
| some ways to prepare alkyl halides |
|
Definition
-radical halogenation of alkanes
-allylic bromination of alkenes
-alkyl halides from alcohols |
|
|
Term
|
Definition
|
|
Term
| stereochemistry with which hydroboration of alkenes occurs |
|
Definition
|
|
Term
| stereochemistry with which oxidation of alkenes occurs |
|
Definition
|
|
Term
| strategies for organic synthesis |
|
Definition
| work backward from the structure of the product, but keep the structure of the starting material in mind |
|
|
Term
|
Definition
| addition of 2 substituents from the same side of the plane |
|
|
Term
|
Definition
| addition of 2 substituents from the same side of the plane |
|
|
Term
| termination of a chain-growth polymerization reaction |
|
Definition
| when 2 radical fragments combine |
|
|
Term
| tertiary ______ can be prepared by the rxn of a tertiary alcohol with HCl, HBr, or HI |
|
Definition
| alkyl chlorides, bromides, or iodides |
|
|
Term
| tertiary alkyl chlorides, bromides, or iodides can be prepared by ______ with HCl, HBr, or HI |
|
Definition
| the rxn of a tertiary alcohol |
|
|
Term
| tertiary alkyl chlorides, bromides, or iodides can be prepared by the rxn of a tertiary alcohol with ______ |
|
Definition
|
|
Term
| the 2 parts of preparation of an alkene |
|
Definition
-dehydrohalogenation
-dehydration |
|
|
Term
| the 3 steps in a chain-growth polymerization reaction |
|
Definition
1: initiation
2: propagation
3: termination |
|
|
Term
| the Diels-Alder rxn forms ______ in a single step |
|
Definition
|
|
Term
| the Diels-Alder rxn occurs by ______, which takes place in a step by a cyclic redistribution of electrons |
|
Definition
|
|
Term
| the Diels-Alder rxn occurs by a pericyclic mechanism, which takes place in a step by a ______ of electrons |
|
Definition
|
|
Term
| the Diels-Alder rxn occurs by a pericyclic mechanism, which takes place in a step by a cyclic redistribution of ______ |
|
Definition
|
|
Term
| the Diels-Alder rxn occurs by a pericyclic mechanism, which takes place in a... |
|
Definition
| step by a cyclic redistribution of electrons |
|
|
Term
| the Simmons-Smith reaction |
|
Definition
| reaction of CH2I2 and Zn-Cu to produce a non-halogenated cyclopropane via a carbenoid reagent |
|
|
Term
| the Simmons-Smith reaction (CH2I2, Zn-Cu) produces ______ via a carbenoid reagent |
|
Definition
| a non-halogenated cyclopropane |
|
|
Term
| the Simmons-Smith reaction (CH2I2, Zn-Cu) produces a non-halogenated cyclopropane via ______ |
|
Definition
|
|
Term
| the Simmons-Smith reaction (______) produces a non-halogenated cyclopropane via a carbenoid reagent |
|
Definition
|
|
Term
| the ______ used in the preparation of alkynes are formed by addition of X2 to alkenes |
|
Definition
|
|
Term
| the bond breakign that causes oxidation in organic chemistry |
|
Definition
|
|
Term
| the bond breaking that causes reduction in organic chemistry |
|
Definition
| breaking C-O, C-N, or C-X bonds |
|
|
Term
| the bond forming that causes oxidation in organic chemistry |
|
Definition
| forming C-O, C-N, or C-X bonds |
|
|
Term
| the bond forming that causes reduction in organic chemistry |
|
Definition
|
|
Term
| the bonds formed in an alkyne triple bond |
|
Definition
| 1 sigma bond and 2 pi bonds |
|
|
Term
| the catalysts most frequently used in hydrogenation of alkenes |
|
Definition
|
|
Term
| the dienes that can undergo the Diels-Alder rxn |
|
Definition
| the dienes that can rotate to achieve an s-cis conformation |
|
|
Term
| the dienes that can't undergo the Diels-Alder rxn |
|
Definition
|
|
Term
| the dihalides used in the preparation of ______ are formed by addition of X2 to alkenes |
|
Definition
|
|
Term
| the dihalides used in the preparation of alkynes are formed by ______ of X2 to alkenes |
|
Definition
|
|
Term
| the dihalides used in the preparation of alkynes are formed by addition of X2 to ______ |
|
Definition
|
|
Term
| the dihalides used in the preparation of alkynes are formed by addition of ______ to alkenes |
|
Definition
|
|
Term
| the intermediate of ______ to alkynes is a vinylic carbocation, which forms less readily than an alkyl carbocation |
|
Definition
|
|
Term
| the intermediate of addition of HX or X2 to ______ is a vinylic carbocation, which forms less readily than an alkyl carbocation |
|
Definition
|
|
Term
| the intermediate of addition of HX or X2 to alkynes is ______, which forms less readily than an alkyl carbocation |
|
Definition
|
|
Term
| the intermediate of addition of HX or X2 to alkynes is a vinylic carbocation, which forms (more or less) readily than an alkyl carbocation |
|
Definition
|
|
Term
| the intermediate of addition of HX or X2 to alkynes is a vinylic carbocation, which forms less readily than ______ |
|
Definition
|
|
Term
| the mechanism by which allylic bromination of alkenes occurs |
|
Definition
| a radical chain mechanism |
|
|
Term
| the mechanism for organometallic coupling rxns is not... |
|
Definition
| a typical polar nucleophilic substitution |
|
|
Term
| the mechanism in Hg(II)-catalyzed additions to alkynes is similar to that of addition to alkenes, but... |
|
Definition
| no NaBH4 is necessary for removal of Hg |
|
|
Term
| the mechanism of ______ involves a four-center, cyclic transition state |
|
Definition
|
|
Term
| the mechanism of hydroboration involves ______ transition state |
|
Definition
|
|
Term
| the molecular orbitals bonding electrons go into |
|
Definition
| the lower molecular orbitals |
|
|
Term
| the most common method of preparing conjugated dienes |
|
Definition
| based-induces addition of allylic halides |
|
|
Term
| the product of the partial reduction of alkynes |
|
Definition
| a more stable trans vinylic anion |
|
|
Term
| the products formed from a terminal alkyne |
|
Definition
|
|
Term
| the products formed from an internal alkyne |
|
Definition
|
|
Term
| the products yielded in rxns of conjugated dienes in electrophilic addition rxns |
|
Definition
both...
-1,2 addition
-1,4 addition |
|
|
Term
| the radical intermediate of an allylic radical is stabilized by... |
|
Definition
|
|
Term
| the ratio of products in ______ of conjugated dienes can vary if the reaction is carried out under conditions of kinetic control or thermodynamic control |
|
Definition
|
|
Term
| the ratio of products in electrophilic addition of ______ can vary if the reaction is carried out under conditions of kinetic control or thermodynamic control |
|
Definition
|
|
Term
| the ratio of products in electrophilic addition of conjugated dienes can vary if the reaction is carried out under conditions of ______ control or ______ control |
|
Definition
|
|
Term
| the reactivity order of different types of H towards chlorination |
|
Definition
| tertiary > secondary > primary |
|
|
Term
| the regiochemistry followed by oxymercuration |
|
Definition
| Markovnikov regiochemistry |
|
|
Term
| the role of water when hypohalous acids are added to alkenes |
|
Definition
|
|
Term
| the rules for naming alkynes are similar to those for naming alkenes, except... |
|
Definition
-the suffix -yne is used for an alkyne
-compounds with both 2bl bonds and triple bonds are enynes
-when there is a choice in numbering, 2bl bonds receive lower numbers than triple bonds
-compounds can also contain alkynyl groups |
|
|
Term
| the rxn conditions of the formation of primary and secondary alkyl chlorides |
|
Definition
| mild, less acidic, and less likely to cause acid-catalyzed rearrangements |
|
|
Term
| the rxn intermediate of alkene halogenation |
|
Definition
| a cyclic halonium intermediate that is formed in a single step by an interaction of an alkene with Br+ or Cl+ |
|
|
Term
| the sequence of steps in radical halogenation of alkanes |
|
Definition
| initiation, propagation, termination |
|
|
Term
| the stability of 1,3-butadiene may be due to... |
|
Definition
| the greater amount of s character of the C-C single bond between the 2bl bonds |
|
|
Term
| the stability order of alkyl radicals |
|
Definition
| tertiary > secondary > primary |
|
|
Term
| the stereochemistry with which catalytic hydrogenation of alkenes occurs |
|
Definition
|
|
Term
| the stereochemistry with which the hydroxylation of alkenes occurs |
|
Definition
|
|
Term
| the stereochemistry with which the hydroxylation of alkenes occurs |
|
Definition
|
|
Term
| the stereochemistry with which the reaction of an alkene with a peroxyacid RCO3H to form an epoxide occurs |
|
Definition
|
|
Term
|
Definition
|
|
Term
| the suffix used for alkyne |
|
Definition
|
|
Term
| the true utility of ozonolysis |
|
Definition
|
|
Term
| the type of stereochemistry halogenation occurs with |
|
Definition
| anti stereochemistry; both halogens come from opposite sides of the molecule |
|
|
Term
| thermodynamic conditions for a rxn |
|
Definition
|
|
Term
|
Definition
| more stable product of a chemical rxn (more stable can be due to less crowded) |
|
|
Term
| treatment of HCCl3 with KOH forms ______ |
|
Definition
|
|
Term
| treatment of HCCl3 with ______ forms dichlorocarbene |
|
Definition
|
|
Term
| treatment of ______ with H2O2 forms 3 molecules of an alcohol |
|
Definition
|
|
Term
| treatment of ______ with KOH forms dichlorocarbene |
|
Definition
|
|
Term
| treatment of ______ with a strong base forms an alkene, with loss of H2O |
|
Definition
|
|
Term
| treatment of an alcohol with ______ forms an alkene, with loss of H2O |
|
Definition
|
|
Term
| treatment of an alcohol with a strong base forms ______, with loss of H2O |
|
Definition
|
|
Term
| treatment of an alcohol with a strong base forms an alkene, with loss of ______ |
|
Definition
|
|
Term
| treatment of the trialkylborane with H2O2 forms ______ |
|
Definition
| 3 molecules of an alcohol |
|
|
Term
| treatment of the trialkylborane with ______ forms 3 molecules of an alcohol |
|
Definition
|
|
Term
| types of reactions of conjugated dienes |
|
Definition
-electrophilic addition to conjugated dienes
-the Diels-Alder cycloaddition reaction
-diene polymers |
|
|
Term
| under conditions of ______ (high temperature), the more stable product (the product whose formation has a larger negative value of ΔG°) forms in greater amounts |
|
Definition
|
|
Term
| under conditions of ______ (lower temp), the product whose formation has the lower energy of activation forms in grater amounts |
|
Definition
|
|
Term
| under conditions of kinetic control (______), the product whose formation has the lower energy of activation forms in grater amounts |
|
Definition
|
|
Term
| under conditions of kinetic control (lower temp), the product whose formation has the ______ forms in grater amounts |
|
Definition
| lower energy of activation |
|
|
Term
| under conditions of thermodyynamic control (______), the more stable product (the product whose formation has a larger negative value of ΔG°) forms in greater amounts |
|
Definition
|
|
Term
| under conditions of thermodyynamic control (high temperature), the ______ product (the product whose formation has a larger negative value of ΔG°) forms in greater amounts |
|
Definition
|
|
Term
| under conditions of thermodyynamic control (high temperature), the more stable product (______) forms in greater amounts |
|
Definition
| the product whose formation has a larger negative value of ΔG° |
|
|
Term
| very strong bases (-NH2) can ______ a terminal alkyne, yielding an acetylide anion |
|
Definition
|
|
Term
| very strong bases (-NH2) can deprotenate ______, yielding an acetylide anion |
|
Definition
|
|
Term
| very strong bases (-NH2) can deprotenate a terminal alkyne, yielding ______ |
|
Definition
|
|
Term
| very strong bases (______) can deprotenate a terminal alkyne, yielding an acetylide anion |
|
Definition
|
|
Term
| vinylic halides give ______ when treated with a strong base |
|
Definition
|
|
Term
| vinylic halides give alkynes when treated with a ______ |
|
Definition
|
|
Term
| water adds to ______ to yield alcohols in the presence of a strong acid catalyst |
|
Definition
|
|
Term
| water adds to alkenes to yield ______ in the presence of a strong acid catalyst |
|
Definition
|
|
Term
| water adds to alkenes to yield alcohols in the presence of ______ |
|
Definition
|
|
Term
| we figure out the sdtructure of then alkyne that yielded the products based on... |
|
Definition
| the oxidation states of specific C's |
|
|
Term
| what a diene must do to undergo the Diels-Alder rxn |
|
Definition
| it must adopt an s-cis ("cis-like") conformation in order to undergo the Diels-Alder rxn |
|
|
Term
| what has higher priority, alkyne or phenyl? |
|
Definition
| aklyne; phenyl is just a substituent |
|
|
Term
| what heat favors in a rxn |
|
Definition
|
|
Term
| what the radical does in the initiation phase of chain-growth polymerization |
|
Definition
| adds to an alkene to generate an alkyl radical |
|
|
Term
| what's more stable: conjugated diene or nonconjugated diene? |
|
Definition
|
|
Term
| when H+ adds to ______, the intermediate carbocation is chiral |
|
Definition
|
|
Term
| when H+ adds to a chiral alkene, the intermediate ______ is chiral |
|
Definition
|
|
Term
| when H+ adds to a chiral alkene, the intermediate carbocation is ______ |
|
Definition
|
|
Term
| when HX and X2 add to alkynes, addition occurs with Makovnikov regiochemistry and ______ stereochemistry |
|
Definition
|
|
Term
| when HX and X2 add to alkynes, addition occurs with ______ regiochemistry and trans stereochemistry |
|
Definition
|
|
Term
| when HX and X2 add to alkynes, addition of 2 equivalents of HX occurs if the ______ is in excess |
|
Definition
|
|
Term
| when HX and X2 add to alkynes, addition of 2 equivalents of HX occurs if the acid is in ______ |
|
Definition
|
|
Term
| when HX and X2 add to alkynes, addition of 2 equivalents of ______ occurs if the acid is in excess |
|
Definition
|
|
Term
| when HX and X2 add to alkynes, addition of ______ of HX occurs if the acid is in excess |
|
Definition
|
|
Term
| when ______ adds to a chiral alkene, the intermediate carbocation is chiral |
|
Definition
|
|
Term
|
Definition
| when the starting and ending energies are roughly the same |
|
|
Term
| when a rxn step is endothermic |
|
Definition
| when it goes from more stable to less stable |
|
|
Term
| when a rxn step is exothermic |
|
Definition
| when it goes from less stable to more stable |
|
|
Term
| when regiochemistry in addition reactions is irrelevant |
|
Definition
| when 2 of the same group is added, such as 2 Br, or when adding groups on a symmetrical alkene |
|
|
Term
| when regiochemistry in addition reactions is irrelevant |
|
Definition
| when 2 of the same group is added, such as 2 Br, or when adding groups on a symmetrical alkene |
|
|
Term
| when regiochemistry in addition reactions is relevant |
|
Definition
| only when adding 2 different groups, such as H and Br, on an unsymmetrical alkene |
|
|
Term
| when regiochemistry in addition reactions is relevant |
|
Definition
| only when adding 2 different groups, such as H and Br, on an unsymmetrical alkene |
|
|
Term
| when the kinetic product wins |
|
Definition
| when you don't let equilibrium be established |
|
|
Term
| when there is a choice in numbering, ______ bonds receive lower numbers than ______ bonds |
|
Definition
|
|
Term
| when water is added to an achiral alkene,... |
|
Definition
| a racemic mixture of products is formed |
|
|
Term
|
Definition
| if there's less entropy on products than on reactants |
|
|
Term
| which product is more stable? kinetic or thermodynamic? |
|
Definition
|
|
Term
| why H peroxide is good against bacteria |
|
Definition
| because it oxidizes some of the membranes in bacteria |
|
|
Term
| why Hg is a good Lewis acid |
|
Definition
| because it has d and f orbitals |
|
|
Term
| why a certain component of a rxn, such as H+, could be on an e'librium arrow |
|
Definition
| because it's both a reactant and product |
|
|
Term
| why a cycloalkene acquires only 1 Br when there's water involved in the reaction |
|
Definition
| because water blocks the addition of another Br |
|
|
Term
| why alkynes tend to be more acidic than alkynes |
|
Definition
| because of the stability and electronegativity of sp C |
|
|
Term
| why an achiral alkene can react to produce a racemic mixture |
|
Definition
-the achiral cationic intermediate can react from either side to produce a racemic mixture
-alternatively, the transition states for top side reaction and bottom side reaction are enantiomers and have the same energy |
|
|
Term
| why cis-trans isomerism is possible in dienes |
|
Definition
| because 2bl bonds remain in the polymer |
|
|
Term
| why hydroboration undergoes non-Markovnikov regiochemistry |
|
Definition
| because of the attachment of B to the less sterically crowded C atom of the alkene |
|
|
Term
| why hydroboration undergoes syn addition |
|
Definition
| because of the four-center, cyclic transition state |
|
|
Term
| why only endo product is formed during the Diels-Alder rxn |
|
Definition
| because orbital overlap is greater in the transition state than for exo product |
|
|
Term
| why the Br in a rxn of an alkene with Br2 could prefer 1 partially positive C over another |
|
Definition
| because 1 C could be more stable than the other |
|
|
Term
| why the intermediate step of the rxn of an alkene with Cl2 contains a Cl atom with 2 bonds to that alkene |
|
Definition
| keeps us from disobeying octet rule |
|
|
Term
| why the mixture of products at the end of an allylic radical rxn is unequal |
|
Definition
| the rxn to form the more substituted 2bl bond is favored |
|
|
Term
| why the reactivity order of different types of H towards chlorination is tertiary > secondary > primary |
|
Definition
| because of bond dissociation energies for formation of the alkyl radicals |
|
|
Term
| whyb hydrogenation of an alkyne to yield an alkene would yield a cis isomer |
|
Definition
| because it's syn addition |
|
|
Term
|
Definition
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|
Term
|
Definition
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|
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