Acyl Halides, Acid Anhydrides, Amines, Amides Flashcards
(27 cards)
acyl halides from carboxylic acids
- reagents and products
SOCl2 (gives acyl halide, HCl, SO2)
PBr3 (gives acyl halide x3, HP3O3)
acyl halide + alcohol = ?
ester
acyl halide + water = ?
carboxylic acid
acyl halide + ammonia = ?
amide
*xs NH3 scavenges HCl
acyl halide + water/ammonia/alcohol reaction type?
addition/elimination
addition/elimination reaction
add nucleophile
eliminate halide
ways to get acid anhydride
- drying
- nucleophilic attack
acid anhydride: from drying
- two carboxylic acids
- P2O5
- removes H2O
acid anhydride: from nucleophilic attack
acyl halide + nucleophile (Na+_desired O-C=O)
acyl halide
contains =O and halide
amine
nitrogen connected to one, two or three r groups (rest H)
amide
contains C=O directly connected to N
imine
N double bonded to C
thiol
R-SH
sulfide/thioether
R-S-R’
ether
R-O-R’
acid anhydride
O=C-O-C=O
acetal
two ethers attached to the same carbon atom
how to get a primary amine
NH3 + alkyl halide
- NH3 attacks C
- Br- takes back a H
*xs NH3 scavenges HBr/HCl
how to get a secondary amine
primary amine + alkyl halide
how to get a tertiary amine
secondary amine + H3C-I
note on getting secondary and tertiary amines
use NaOH in second step to quench reaction
-instead of I-/Br- etc
how to get a primary amide
acyl halide + ammonia
how to get a secondary amide
acyl halide + primary amine
