T3 Reactions Spivak Flashcards
Carboxylic acid –> Ester
2HCl and ROH
Transesterification
A) Base ether (NaH WES -OR’)
B) 2HCl and R’OH
Ester –> Amide
NHR2 (amine) and B-
Amide –> Carboxylic Acid
A) Base (OH- with anion product)
B) 2HCl and water
Acid Chloride –> Carboxylic Acid
Water, TEA
Carboxylic Acid –> Acid Chloride
SOCl2
Acid Chloride –> Ester
ROH and TEA
Acid Chloride –> Amide
HNR2 and TEA
Ester –> Carboxylic Acid (anion)
- Use OH- base (also deprotonates product)
2. Use 2HCl and a water
Acid Chloride –> Anhydride
NaH, Carboxylic Acid -(R’)
Anhydride –> Ester (+CA)
ROH (H+ transfer)
Carboxylic Acid –> Anhydride
NaH
Acid Chloride
Anhydrides –> Amide
(2) H2NR
Carboxylic acid –> Amide
DCC
Amine
Carboxylic Acid –> Ester (better way)
DCC / DMAP
ROH
Acid Chloride –> Isocyanate
Curtis rearr.
NaN3
Isocyanate –> Amine
2 H2O
Isocyanate –> Carbamate (Urethane)
ROH
Isocyanate –> Urea
R2NH
Phosgene –> Urea
2 HNR2
2 TEA
Phosgene –> Carbonate
2 ROH
2 TEA
Phosgene –> Carbamate
1 ROH
1 HNR2
2 TEA
Acid Chloride –> Alcohol
LiAlH4
H2O
Ester/Anhydride –> Alcohol
LiAlH4
H2O
Acid Chloride –> Aldehyde
DA MONSTA
Water
Ester –> Aldehyde
DIBAL (Diisobutylaluminum hydride)
Water
Acid Chloride/ Esters –> 3° Alcohol
Grignard and water work up
Acid Chloride –> Ketone
Cuprate (CuR2Li) and water work up
Amide –> Amine
LiAlH4
H2O
Carboxylic acid –> Alkyl halide
Hunsdieker
Ag2O
Br2
Alkyl bromide –> CA
CO2
Mg
Water work up
Nitriles –> Alkylhalides
NaCN
Nitriles –> CA
H3O+
H2O