Carboxylic Acid Derivatives Rnxs Flashcards
1
Q
Hydrolysis of acid chlorides
A
COCl + H20 -> COOH + HCl
- most reactive
2
Q
Hydrolysis of acid anhydrides
A
Anhydride + H20 -> 2COOH
- 2nd most reactive
3
Q
Ester hydrolysis
A
- very slow rxn even at high temperatures
- acidic or basic (saponification) conditions are needed
Ester + H20 + H-A/A -> COOH + OH - 2nd least reactive
4
Q
Amine hydrolysis
A
- require very vigorous conditions in either acid or base
In HCl: amide + H20 -> COOH + NH4+ + Cl-
In NaOH: amide + H20 -> COONa+ + NH3 - least reactive
5
Q
Acid chloride plus alcohol
A
COCl + OH -> COOR + HCl
- most reactive
6
Q
Acid anhydride plus alcohol
A
- one part ester and one past acid is obtained
Anhydride + OH -> COOR + COOH - most reactive
7
Q
Ester plus alcohol
A
- undergo an exchange reaction called transesterification (r groups switch)
- requires acid catalysis
COOR1 + R2OH -> COOR2 + R1OH - 2nd least reactive
8
Q
Amide plus alcohol
A
NOPE
9
Q
Acid chloride plus amine
A
- requires 2 mols of the amine
COCl + 2NH3 -> CONH2 + NH4+ + Cl- - most reactive
10
Q
Acid anhydride plus amine
A
- forms an amide with a carboxylate by product
- requires 2 molar equivalent of the amine
Acid anhydride + NH3 -> CONH2 + COOH - 2nd most reactive
11
Q
Ester plus amine
A
- lower reactivity as alkoxides (RO) are poor leaving groups
COOR + NH3 -> CONH2 + ROH - 2nd least reactive
12
Q
Amide plus amine
A
NOPE
13
Q
Carboxylic acid to acid chloride
A
COOH + SOCl2 -> COCl
14
Q
Acid chloride to Carboxylic acid
A
COCl + H20 -> COOH
15
Q
Ester plus Grignard reagent
A
- 2M equivalent of reagent is required
- COOCH3 + 2CH3CH2-MgBr -> Hydroxyl group and two ethyl groups attached to C atom
