780 CHAPTER 18 Carbonyl Compounds II
- List the following compounds in order of decreasing reactivity toward nucleophilic attack:
- a. Show the reagents required to form the primary alcohol.
b. Which of the reactions cannot be used for the synthesis of isobutyl alcohol?
c. Which of the reactions changes the carbon skeleton of the starting material?- Using cyclohexanone as the starting material, describe how each of the following compounds could be synthesized:
a. d. g.b. e. h.c. f. i.- Propose a mechanism for the following reaction:
- List the following compounds in order of decreasing for hydrate formation:
ClCOO 2 N CH 3 OCH 3COCH 3COCH 3COCH 3KeqHOCH 2 CH 2 CH 2 CH (^2) OCH 3
HCl
CH 3 OH
O
O
C
H
CH 2 CH 3
(show two methods)
Br N(CH 3 ) 2
(show two methods)
CH 2 NH 2
OH NH 2 CH CH 2
∆
RCH 2 OH
O
R C R′CH CH 2
H 2 C O
RCH 2 Br
RCH 2 OCH 3
H
O
ROHC
O
RORC
O
RClC
O
O C
O
RRC
O
CH 3 CH 2 CHCCH 2 CH 3
O
CH 3
CH 3 CH 2 CHCCCH 2 CH 3
O
CH 3 CH 3
CH 3
CH 3 CHCH 2 CCH 2 CH 3
O
CH 3
CH 3 CH 2 CHCCHCH 2 CH 3
O
CH 3 CH 2 CCH 2 CH 3
O
CH 3 CH 3
CH 3 CH 2 CH
O