Problems 725
b. Which of the reactions that do not occur can be made to occur if an acid catalyst is added to the reaction mixture?
- 1,4-Diazabicyclo[2.2.2]octane (abbreviated DABCO) is a tertiary amine that catalyzes transesterification reactions. Propose a
mechanism to show how it does this.
- Identify the major and minor products of the following reaction:
- Two products, A and B, are obtained from the reaction of 1-bromobutane with Compound A reacts with acetyl chloride to
form C, and B reacts with acetyl chloride to form D. The IR spectra of C and D are shown. Identify A, B, C, and D.
- Phosgene was used as a poison gas in World War I. Give the product that would be formed from the reaction of phosgene
with each of the following reagents:
- one equivalent of methanol 3. excess propylamine
- excess methanol 4. one equivalent of ethanol followed by one equivalent of methylamine
- When Ethyl Ester treated butanedioic acid with thionyl chloride, she was surprised to find that the product she obtained was an
anhydride rather than an acyl chloride. Propose a mechanism to explain why she obtained an anhydride.
(COCl 2 )
2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16
380036003400320030002800260024002200 2000 1800 1600 1400 1200 1000 800 600
Compound D
Wavenumber (cm−^1 )
% Transmittance
2.5
4000
2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16
380036003400320030002800260024002200 2000 1800 1600 1400 1200 1000 800 600
Compound C
Wavenumber (cm−^1 )
% Transmittance
2.5
4000
NH 3.
CH 2 OH
CH 2 CH 3 + CH 3 CCl
N
H
O
NN
1,4-diazabicyclo[2.2.2]octane
DABCO
O O O
CH 3 CCl + 10.CH 3 COCH 3 + CH 3 OH CH 3 COCH 3
O
CH 3 COH
O
- H 2 O
CH 3 CNHCH 3 +
O
CH 3 COH
O
CH 3 CNHCH 3 + 9. H 2 O
O
CH 3 COCCH 3
O O
CH 3 CO−
O
7.
