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TitleMCAT Organic Summary Sheet
TagsIsomer Amine Alkene Organic Chemistry Chirality (Chemistry)
File Size666.6 KB
Total Pages6
Document Text Contents
Page 5

R

O

H

OH

H

OOH

H

H

R

mild base

The aldol condensation between two aldehydes to give a -hydoxy aldehyde

O

HR

O

HR

OH
aldol products can dehydrate under acidic
or basic conditions to give the conjugated product

O

H

O

H3C

O

HO

H

1

2

3

4

5 1
2

3

4 5

aldol reactions can occur intramoleuclarly to give
cyclic products (favouring 5 or 6 membered rings)

R

O

OEt

OH

OEt

OO

OEtR

mild base

Claisen condensation is similar to the aldol reaction, with esters as the starting material

Michael Addition

OO LDA

THF

-78
o
C

O
-

O
-

Li
+

O

H2O

OH

O

O

O

Carboxylic Acid

R

O

OH

R OH

R

O

R
C

N

H

CrO 3

CrO 3

H+/ H2O

LiAlH4

R

O

O

R

O

O

R

O

N
H

R

O

R'

R'

H+/heat

R'OH
H+

R'NH2
H+

H2O

H2O

H2O

+

+

+

alcohols

aldyhydes

nitriles

anhydrides

esters

amides

carboxylic
acids

R

O

Cl

SOCl2

acid chlorides

R

O

Nu

 Nu Nucleophilic acyl
substitutions

 Ami nes
Basicity Review

 A base is an atom with a lone pair of electrons. The best bases are
negatively charged.

RCH2

 _   _ 
R 2 N> R 3 N> RNH2>

N

NH2

> >

O

R NR2

> ROH > NR 4
+

>OH >
 _ 

O
H+

N

R

Reductive Aminolysis

+ H2 NR 

1o amine
+ H2O

(know this forward
and backwards)

an imine or Schiff base

O

H
N

N

H
+

a s e c o n d a r y
a m in e

a n e n a m i n e

Hoffmann Elimination:

CH3(CH2)5 NH2
CH3I

(excess)
CH3(CH2)5 N(CH3)3I

Ag2O

H2O, heat
CH3(CH2)3CH CH2  + N(CH3)3

1-Hexene (60%)
Hexyltrimethyl-
ammonium iodide

Hexylamine

Diazotization Reaction :

 NH2

+ HNO2 + H2SO4

 N
 N

HSO4 + 2 H2O

O
NH 2NH 2

KOH
W ol f f-K ischner reduc t ion

Diazonium Coupling Reaction:

 N N HSO4 Y  N

An azo compoundwhere Y = OH or NR 2

 N

(E)

Y

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