Problems 723- Name the following compounds:
a. e. h.b. f. i.c. g. j.d.- What products would be formed from the reaction of benzoyl chloride with the following reagents?
a. sodium acetate e. aqueous NaOH h. 4-chlorophenol
b. water f. cyclohexanol i. isopropyl alcohol
c. dimethylamine g. benzylamine j. aniline
d. aqueous HCl - a. List the following esters in order of decreasing reactivity in the first step of a nucleophilic acyl substitution reaction (formation
of the tetrahedral intermediate):
b. List the same esters in order of decreasing reactivity in the second step of a nucleophilic acyl substitution reaction (collapse of
the tetrahedral intermediate).- a. Which compound would you expect to have a higher dipole moment, methyl acetate or butanone?
b. Which would you expect to have a higher boiling point?- How could you use spectroscopy to distinguish among the following esters?
- If propionyl chloride is added to one equivalent of methylamine, only a 50% yield of N-methylpropanamide is obtained. If,
however, the acyl chloride is added to two equivalents of methylamine, the yield of N-methylpropanamide is almost 100%.
Explain these observations. - a. When a carboxylic acid is dissolved in isotopically labeled water the label is incorporated into both oxygens of the
acid. Propose a mechanism to account for this.
b. If a carboxylic acid is dissolved in isotopically labeled methanol and an acid catalyst is added, where will the label
reside in the product?- What reagents would you use to convert methyl propanoate into the following compounds?
a. isopropyl propanoate c. N-ethylpropanamide
b. sodium propanoate d. propanoic acid
(CH 3 18 OH)+ H 2 O
CH 3 OH18
+ H 2 O
CH 3 OH1818COCO(H 2 O^18 ),ABCDCH 3 COCH 2 CH 3OHCOCH 2 CH 2 CH 3OCH 3 CH 2 COCH 3OHCOCHCH 3O CH 3(^1) H NMR
CH 3 COCH 3
methyl acetate
O
CH 3 CCH 2 CH 3
butanone
O
CH 3 CO
O
CH 3 CO
O
CH 3 CO CH 3
O
CH 3 CO Cl
O
AB C D
CH 3 CH 2 COCCH 2 CH 3
O O
C
CH 3
CH 2 CN
H
CH 2 CH 2 CH 3
COCCH 3
O O
CH 3 CH 2 CH 2 CH 2 CN
C
CH 3
CH 2 CH 3
H
CH 2 COOH
CH 3 CH 2 CH 2 CH 2 CCl
O
CH 3 CH 2 COCH 2 CH 2 CH 3
O
CH 2 CHCH 2 CNHCH 3
O
CH 3 CH 2 CH 2 CN(CH 3 ) 2
O
CH 3 CH 2 CHCH 2 CH 2 CH 2 COH
CH 2 CH 3 O