1
Organic Chemistry Summary Contents
Compiled by Romy Stevens, May 2022, for CEM2005W at the University of Cape Town
Contents
Organic Chemistry Summary Contents ................................................................................................... 1
Organic Chemistry Summary .................................................................................................................. 2
Nucleophilic 1-2-addition at carbonyl groups..................................................................................... 2
Nucleophilic addition to aldehydes and ketones ............................................................................ 2
Nucleophilic substitution at carbonyl groups ..................................................................................... 3
Carboxylic acid derivatives .............................................................................................................. 3
Reactions of acid anhydrides and acid chlorides ............................................................................ 4
Chemistry of esters ......................................................................................................................... 4
Imines and enamines ...................................................................................................................... 5
Identify reagents and solvents ............................................................................................................ 5
Reagents.......................................................................................................................................... 5
Solvents ........................................................................................................................................... 5
Functional groups (identify) ................................................................................................................ 6
Vocabulary .......................................................................................................................................... 7
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Organic Chemistry Summary
N.B. Any nucleophilic attacks at carbonyl carbons in this document, imply that the C=O double bond
electrons will go and sit on the oxygen.
Nucleophilic 1-2-addition at carbonyl groups
Nucleophilic addition to aldehydes and ketones
Reactants Products Mechanism
Aldehydes
Secondary Cr2O72- Ketones Jones oxidation
alcohol (deprotonate and add
C=O bond)
A and K Cyanide ion Sp3 carbon with CN and OH Cyanide nucleophile
(H2O, HCl) attached (cyanohydrin) attacks carbonyl
group, oxygen gets
protonated
cyanohydrin NaOH, H2O A or K Reverse: base
deprotonates –OH,
oxygen charge forms
double bond, kicks
out CN-
A and K 1) NaBH4 (LiAlH4) A: 1° alcohol Hydride nucleophile
2) H2O, MeOH K: 2° alcohol attacks carbonyl
group,
Negative oxygen
claims an H from
water
A and K Alcohols (catalyst) Hemiacetals, acetals Protonated alcohol
nucleophile attacks
carbonyl carbon,
alcohol branch loses
an H, oxygen branch
gains an H
➔ hemiacetals Alcohols (catalyst) acetals Repeat, -OH group
replaced by alcohol -
OR
➔ hemiacetals Alcohols (catalyst) Oxonium ion -OR oxygen forms
double bond, now O+,
Loss of carbonyl
oxygen
A and K amines Hemi-aminals Protonated amine
nucleophile attacks
carbonyl carbon,
amine group loses an
H, oxygen branch
gains an H
➔ hemiaminal amine Imine and water -NHR forms double
bond, now N+, Loss of
carbonyl oxygen
Organic Chemistry Summary Contents
Compiled by Romy Stevens, May 2022, for CEM2005W at the University of Cape Town
Contents
Organic Chemistry Summary Contents ................................................................................................... 1
Organic Chemistry Summary .................................................................................................................. 2
Nucleophilic 1-2-addition at carbonyl groups..................................................................................... 2
Nucleophilic addition to aldehydes and ketones ............................................................................ 2
Nucleophilic substitution at carbonyl groups ..................................................................................... 3
Carboxylic acid derivatives .............................................................................................................. 3
Reactions of acid anhydrides and acid chlorides ............................................................................ 4
Chemistry of esters ......................................................................................................................... 4
Imines and enamines ...................................................................................................................... 5
Identify reagents and solvents ............................................................................................................ 5
Reagents.......................................................................................................................................... 5
Solvents ........................................................................................................................................... 5
Functional groups (identify) ................................................................................................................ 6
Vocabulary .......................................................................................................................................... 7
, 2
Organic Chemistry Summary
N.B. Any nucleophilic attacks at carbonyl carbons in this document, imply that the C=O double bond
electrons will go and sit on the oxygen.
Nucleophilic 1-2-addition at carbonyl groups
Nucleophilic addition to aldehydes and ketones
Reactants Products Mechanism
Aldehydes
Secondary Cr2O72- Ketones Jones oxidation
alcohol (deprotonate and add
C=O bond)
A and K Cyanide ion Sp3 carbon with CN and OH Cyanide nucleophile
(H2O, HCl) attached (cyanohydrin) attacks carbonyl
group, oxygen gets
protonated
cyanohydrin NaOH, H2O A or K Reverse: base
deprotonates –OH,
oxygen charge forms
double bond, kicks
out CN-
A and K 1) NaBH4 (LiAlH4) A: 1° alcohol Hydride nucleophile
2) H2O, MeOH K: 2° alcohol attacks carbonyl
group,
Negative oxygen
claims an H from
water
A and K Alcohols (catalyst) Hemiacetals, acetals Protonated alcohol
nucleophile attacks
carbonyl carbon,
alcohol branch loses
an H, oxygen branch
gains an H
➔ hemiacetals Alcohols (catalyst) acetals Repeat, -OH group
replaced by alcohol -
OR
➔ hemiacetals Alcohols (catalyst) Oxonium ion -OR oxygen forms
double bond, now O+,
Loss of carbonyl
oxygen
A and K amines Hemi-aminals Protonated amine
nucleophile attacks
carbonyl carbon,
amine group loses an
H, oxygen branch
gains an H
➔ hemiaminal amine Imine and water -NHR forms double
bond, now N+, Loss of
carbonyl oxygen
