Term
| rules for naming alkyl halides |
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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 |
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Term
| some alkyl halides are named by first citing the ______ and then citing the ______ |
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Definition
name of the alkyl group
halogen |
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Term
| geometry of alkyl halides |
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Definition
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Term
| bond length in alkyl halides vs. size of halogen bonded to the C |
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Definition
directly proportional
bond lengths increase with increasing size of the halogen |
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Term
| bond strength in alkyl halides vs. size of halogen bonded to the C |
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Definition
inversely proportional
bond strengths decrease with increasing size of the halogen |
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Term
| Carbon-halogen bonds are... |
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Definition
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Term
| many halomethanes have... |
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Definition
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Term
| alkyl halides behave as ______ in polar rxns |
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Definition
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Term
| alkyl halides behave as electrophiles in ______ rxns |
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Definition
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Term
| some ways to prepare alkyl halides |
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Definition
-radical halogenation of alkanes
-allylic bromination of alkenes
-alkyl halides from alcohols |
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Term
| the sequence of steps in radical halogenation of alkanes |
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Definition
| initiation, propagation, termination |
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Term
| radical halogenation of alkanes continues to produce... |
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Definition
| di- and polysubstituted products |
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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 |
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Definition
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Term
| if more than 1 type of H is present during the radical halogenation of an alkane,... |
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Definition
| more than 1 type of monosubstituted product is formed |
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Term
| the reactivity order of different types of H towards chlorination |
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Definition
| tertiary > secondary > primary |
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Term
| why the reactivity order of different types of H towards chlorination is tertiary > secondary > primary |
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Definition
| because of bond dissociation energies for formation of the alkyl radicals |
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Term
| the stability order of alkyl radicals |
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Definition
| tertiary > secondary > primary |
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Term
| rxn of ______ with NBS causes bromination at the position allylic to the 2bl bond |
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Definition
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Term
| rxn of an alkene with ______ causes bromination at the position allylic to the 2bl bond |
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Definition
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Term
| rxn of an alkene with NBS causes ______ |
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Definition
| bromination at the position allylic to the 2bl bond |
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Term
| the mechanism by which allylic bromination of alkenes occurs |
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Definition
| a radical chain mechanism |
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Term
| how the radical chain mechanism occurs in allylic bromination of alkenes |
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Definition
| 1: Br• abstracts an allylic H
2: the allylic radical reacts with Br2 to form an allylic bromide, plus Br• |
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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 |
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Definition
| allylic bromination of alkenes |
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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 |
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Definition
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Term
| allylic bromination of alkenes occurs at the allylic position because... |
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Definition
| an allylic C-H bond is weaker than most other C-H bonds, and the allylic radical is more stable |
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Term
| reasons for stability of an allylic radical |
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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 |
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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 |
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Definition
| C with the unpaired electron |
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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 |
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Definition
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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 |
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Definition
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Term
| in an allylic radical, the C with the unpaired electron is sp2 hybridized, and its p orbital can overlap with ______ |
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Definition
| the p orbitals of the 2bl bond C's |
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Term
| the radical intermediate of an allylic radical is stabilized by... |
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Definition
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Term
| how resonance stabilizes allylic radicals |
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Definition
| because the unpaired electron is spread out over an extended pi network |
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Term
| rxn of the allylic radical with Br2 can occur at... |
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Definition
| either end of the pi orbital system |
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Term
| a mixture of products may form at the end of an allylic radical rxn if... |
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Definition
| the alkene is unsymmetrical |
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Term
| why the mixture of products at the end of an allylic radical rxn is unequal |
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Definition
| the rxn to form the more substituted 2bl bond is favored |
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Term
| products of allylic bromination reactions can be ______ to form dienes |
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Definition
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Term
| products of allylic bromination reactions can be dehydrohalogenated to form ______ |
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Definition
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Term
| ______ alkyl chlorides, bromides, or iodides can be prepared by the rxn of a tertiary alcohol with HCl, HBr, or HI |
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Definition
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Term
| tertiary ______ can be prepared by the rxn of a tertiary alcohol with HCl, HBr, or HI |
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Definition
| alkyl chlorides, bromides, or iodides |
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Term
| tertiary alkyl chlorides, bromides, or iodides can be prepared by ______ with HCl, HBr, or HI |
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Definition
| the rxn of a tertiary alcohol |
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Term
| tertiary alkyl chlorides, bromides, or iodides can be prepared by the rxn of a tertiary alcohol with ______ |
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Definition
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Term
| reaction of ______ alcohols occurs under more drastic conditions, which may destroy other acid-sensitive functional groups |
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Definition
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Term
| reaction of secondary or primary alcohols occurs under ______, which may destroy other acid-sensitive functional groups |
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Definition
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Term
| reaction of secondary or primary alcohols occurs under more drastic conditions, which may... |
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Definition
| destroy other acid-sensitive functional groups |
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Term
| ______ can be formed by treatment of the corresponding alcohols with SOCl2 or PBr3, respectively |
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Definition
| primary and secondary alkyl chlorides and bromides |
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Term
| primary and secondary alkyl chlorides and bromides can be formed by ______ with SOCl2 or PBr3, respectively |
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Definition
| treatment of the corresponding alcohols |
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Term
| primary and secondary alkyl chlorides and bromides can be formed by treatment of the corresponding alcohols with ______ |
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Definition
| SOCl2 or PBr3, respectively |
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Term
| the rxn conditions of the formation of primary and secondary alkyl chlorides |
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Definition
| mild, less acidic, and less likely to cause acid-catalyzed rearrangements |
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Term
| ______ can be prepared using either (CH3CH2)2 NSF3 or HF in a pyridine |
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Definition
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Term
| alkyl fluorides can be prepared using either ______ or ______ in a pyridine |
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Definition
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Term
| alkyl fluorides can be prepared using either (CH3CH2)2 NSF3 or HF in a ______ |
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Definition
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Term
| organohalides react with Mg to produce... |
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Definition
| organimagnesium halides (RMgX) |
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Term
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Definition
| organomagnesium halides, RMgX |
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Term
| ______ can be formed from alkyl, alkenyl, and aryl halides |
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Definition
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Term
| Grignard reagents can be formed from ______ |
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Definition
| alkyl, alkenyl, and aryl halides |
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Term
| is steric hinderance a barrier to the formation of Grignard reagents? |
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Definition
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Term
| in Grignard reagents, the ______ bonded to Mg is negatively polarized and is nucleophilic |
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Definition
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Term
| in Grignard reagents, the C bonded to ______ is negatively polarized and is nucleophilic |
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Definition
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Term
| in Grignard reagents, the C bonded to Mg is ______ and is nucleophilic |
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Definition
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Term
| in Grignard reagents, the C bonded to Mg is negatively polarized and is ______ |
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Definition
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Term
| Grignard reagents react with ______ to form hydrocarbons |
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Definition
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Term
| Grignard reagents react with weak acids to form ______ |
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Definition
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Term
| ______ can react with Li to form alkyllithiums |
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Definition
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Term
| alkyl halides can react with ______ to form alkyllithiums |
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Definition
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Term
| alkyl halides can react with Li to form ______ |
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Definition
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Term
| ______ can combine with CuI to form lithium diorganocopper compounds (R2CuLi), which are known as Gilman reagents |
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Definition
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Term
| alkyllithiums can combine with ______ to form lithium diorganocopper compounds (R2CuLi), which are known as Gilman reagents |
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Definition
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Term
| alkyllithiums can combine with CuI to form ______, which are known as Gilman reagents |
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Definition
| lithium diorganocopper compounds (R2CuLi) |
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Term
| alkyllithiums can combine with CuI to form lithium diorganocopper compounds (R2CuLi), which are known as ______ |
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Definition
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Term
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Definition
| lithium diorganocopper compounds (R2CuLi) |
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Term
| ______ can react with alkyl halides (except for fluorides) to form hydrocarbon products |
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Definition
| lithium diorganocopper compounds (R2CuLi) |
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Term
| lithium diorganocopper compounds (R2CuLi) can react with ______ (except for fluorides) to form hydrocarbon products |
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Definition
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Term
| lithium diorganocopper compounds (R2CuLi) can react with alkyl halides (except for ______) to form hydrocarbon products |
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Definition
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Term
| lithium diorganocopper compounds (R2CuLi) can react with alkyl halides (except for fluorides) to form ______ |
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Definition
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Term
| ______ rxns are useful for forming large molecules from small pieces |
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Definition
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Term
| organometallic coupling rxns are useful for ______ |
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Definition
| forming large molecules from small pieces |
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Term
| organometallic coupling rxns can be carried out on... |
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Definition
| alkyl, vinyl, and aryl halides |
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Term
| the mechanism for organometallic coupling rxns is not... |
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Definition
| a typical polar nucleophilic substitution |
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Term
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Definition
| Pd catalyzed coupling of aryl or vinyl organotin reagents with organohalides |
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Term
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Definition
| a rxn that results in a loss of electron density by a C |
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Term
| oxidation of a C may be due to... |
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Definition
-bond formation between C and more eneg atom (usually O, N, or halogen)
-bond breaking between C and less eneg atom (usually H) |
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Term
| examples of oxidation of a C include ______ and reduction of alkenes with Br2 |
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Definition
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Term
| examples of oxidation of a C include chloronation of alkanes and ______ |
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Definition
| reduction of alkenes with Br2 |
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Term
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Definition
| rxn that results in a gain of electron density by a C |
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Term
| reduction of a C may be due to... |
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Definition
-bond formation between C and less eneg atom
-bond breaking between C and more eneg atom |
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Term
| examples of reduction of a C include ______, and reduction of an alkene with H2 |
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Definition
| conversion of a Grignard reagent to an alkene |
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Term
| examples of reduction of a C include conversion of a Grignard reagent to an alkene, and ______ |
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Definition
| reduction of an alkene with H2 |
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Term
| ______ is/are at the lowest oxidation level and ______ is/are at the highest level |
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Definition
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Term
| a rxn that converts a compound from a lower oxidation level to a higher oxidation level is... |
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Definition
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Term
| a rxn that converts a compound from a higher oxidation level to a lower oxidation level is... |
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Definition
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Term
| cations typically form under (acidic or basic) conditions |
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Definition
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Term
| anions typically form under (acidic or basic) conditions |
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Definition
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