Organic Chemistry

Problems 785

65. What carbonyl compound and what phosphonium ylide are needed to synthesize the following compounds?

a. b. c. d.

66. Identify compounds A and B:


67. Propose a reasonable mechanism for each of the following reactions:

a.

b.

68. A compound reacts with methylmagnesium bromide followed by acidification to form the product with the following
    spectrum. Identify the compound.


69. Show how each of the following compounds can be prepared from the given starting material. In each case, you will need to use a
    protecting group.

a. c.

b.

Cl

OH

COOH

OH

C

CH 3 CH 3

OO

Br CH 2 CH 2 OH

C

CH 3 CHCH 2 COCH 3

O

OH

CH 3 CHCH 2 CCH 3

CH 3

OH OH

87654 3210

frequency

δ (ppm)

(^1) H NMR
HH

• OH O
  NH
  OH
  N
  C
  HCl
  O
  O
  O
  CH 3 O CH 3 O
  ∆
  A CH 2 CHCCH 2 CHCH 3

1. (CH 2
   2. H 3 O+

CH 3

CH 3

OH

CH) 2 CuLi

B

1. CH 3 Li
   2. H 3 O+

CH CH CH 2

CHCH 2 CH 3

CH CHCH 2 CH 2 CH 3