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Reaction mechanisms
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Organic Chemistry
Undergraduate 2
11/21/2011

Additional Organic Chemistry Flashcards

 


 

Cards

Term
Alkene --HX-->
Definition

-Adds X to most subbed

-Adds H to least subbed

 

-Haloalkane

Term
Alkene  ---H2SO4, H2O-->
Definition

-Adds OH to most subbed

-Adds H to least subbed

 

-Alkanol

Term
Alkene  ---X2, CH2Cl2-->
Definition

-Adds trans X's to each double bond carbon

 

-Dihaloalkane

Term
Alkene  ---Br2/H2O--->
Definition

-Trans addition

-X to least subbed

-OH to most subbed

 

-haloalkanol

Term
Alkene  ---1. Hg(OAc)2, H2O  2. NaBH4-->
Definition

-OH added to most subbed

-H added to least subbed

 

-alkanol

 

Term
Alkene  ---1. BH3 2. H2O2, NaOH--->
Definition

-OH added to least subbed

-H added to most subbed

 

-alkanol

Term
Alkene  ----1. OsO4 2. NaHSO3, H2O--->
Definition

-Cis OH's added to double bond carbons

 

-alkandiol

Term
Alkene  ---1.O3  2. (Ch3)2S--->
Definition

-Cleaves double bond

-adds =O where dbl bond was

-Keto/enol tautomers

 

-ethers and aldehydes

Term
alkene  ------H2, Pt------>
Definition

-double bond reduced and H's added

 

-alkane

Term
Terminal alkyne  -----NaNH2----->
Definition

-Removes terminal H and creates anion

-can add to chain length with haloalkane

 

-akyne anion

Term
Alkene --X2-->        ----NaNH2 in NH3(l)--->
Definition

-rxn 1 yields dihaloalkane

-rxn 2 yields alkyne

 

-alkyne

Term
Alkyne  ---X2-->        ---X2------>
Definition

-Rxn 1 yields trans dihaloalkene

-Rxn 2 yields tetrahaloalkane

 

-tetrahaloalkane

Term
Alkyne  ----HX---->       ------HX----->
Definition

-Rxn 1 yields haloalkene on most subbed

-H added to least subbed

 

-Rxn 2 yields dihaloalkane on the most subbed

-H added to least subbed

 

-dihaloalkane

Term
Internal alkyne -----1.BH3 2.H2O2, NaOH--->
Definition

-OH added to either carbon

-Keto/enol tautomerization

 

-ketone

Term
Terminal alkyne  ----1.(sia)2BH  2.H2O2, NaOH--->
Definition

-OH added to least subbed

-Keto/enol tautomerization

 

-aldehyde

Term
Alkyne  ----H2SO4, HgSO4, H2O----->
Definition

-OH added to most subbed

-H to least subbed

-Keto/enol tautomerization

 

-ketone or aldehyde

Term
Alkyne   ----H2, Pt------->
Definition

-H's added to all bonds

-reduced all the way

 

-alkane

Term
Alkyne  -----H2, Lindlar------>
Definition

-Syn H's added

-Only one reduction step

 

-cis alkene

Term
Alkyne  -----1.BH3 2.CH3COOH----->
Definition

-syn H's added to triple bond

 

-cis alkene

Term
Alkyne  ------Na in NH3(l)------>
Definition

-Anti H's added to triple bond

-only 1 reduction step

 

-trans alkene

Term
Alkane  -------X2, hv------>
Definition

-X replaces most subbed C's H

 

-haloalkane

Term
Alkyne  ----NBS, CH2Cl2, hv---->
Definition
-Br replaces H on allylic C
Term
Alkene  -----O2, R•------->
Definition
-OOH replaces H on allylic Carbon
Term
Alkene  -----HBr, Peroxides----->
Definition

-double bond breaks

-H added to most subbed

-Br added to least subbed

 

-haloalkane

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