726 CHAPTER 17 Carbonyl Compounds I
- Give the products of the following reactions:
a. f.
b. g.
c. h.
d. i.
e. j.
- When treated with an equivalent of methanol, compound A, with molecular formula forms the compound whose
NMR spectrum is shown below. Identify compound A. - a. Identify the two products obtained from the following reaction:
b. Eddie Amine carried out the preceding reaction, but stopped it before it was half over, whereupon he isolated the major
product. He was surprised to find that the product he isolated was neither of the products obtained when the reaction was
allowed to go to completion. What product did he isolate?
- An aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major product.
However, if the amine is tertiary, an amide is not formed. What product isformed? Explain. - a. Ann Hydride did not obtain any ester when she added 2,4,6-trimethylbenzoic acid to an acidic solution of methanol. Why?
(Hint:Build models.)
b. Would Ann have encountered the same problem if she had tried to synthesize the methyl ester of p-methylbenzoic acid in the
same way?
c. How could she prepare the methyl ester of 2,4,6-trimethylbenzoic acid? (Hint:See Section 16.12.)
CH 3 COCCH 3 CH 3 CHCH 2 CH 2 OH
excess
+
O O NH 2
87654 3210
δ (ppm)
frequency
(^1) H
C 4 H 6 Cl 2 O,
- CH 3 OH
excess
HCl
O
O
O
ClCCl
OH
OH
O
- NH 3
excess
O
O - H 2 O O
O
O
O
CH 2 COH
COH
(CH 3 C) 2 O
∆
O
O
O
COH
- SOCl 2
- 2 CH 3 NH 2
O
CH 3 CCH 2 OCCH 3 CH 3 OH
excess
CH 3 O−
+
O O
NH H
2 O
HCl
+
O
O H
2 O
excess
+
O
HCl
CH 3 CCl + KF
O