Organic Chemistry Reactions Summary: Nucleophilic addition and substitution
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Course
CEM2005W (CEM2005W)
Institution
University Of Cape Town (UCT)
organised, colour coded word document with small diagrams and descriptions of mechanisms in words.
All reactions are tabulated showing reagents, products, and mechanism for each reaction
Contents:
Organic Chemistry Summary;
Nucleophilic 1-2-addition at carbonyl groups;
Nucleophilic addition ...
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
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