Organic Chemistry

782 CHAPTER 18 Carbonyl Compounds II

51. Propose a mechanism for each of the following reactions:

a. c.

b.

52. How many signals would the product of the following reaction show in these spectra

a. its spectrum

b. its spectrum

53. Give the products of the following rections. Show all stereoisomers that are formed.

a. c.

b. d.

54. List three different sets of reagents (a carbonyl compound and a Grignard reagent) that could be used to prepare each of the
    following tertiary alcohols:

a. b.

55. Give the product of the reaction of 3-methyl-2-cyclohexenone with each of the following reagents:
    a. followed by d. HBr
    b. excess NaCN, HCl e. followed by
    c. Pd f.


56. Norlutin and Enovid are ketones that suppress ovulation. Consequently, they have been used clinically as contraceptives. For
    which of these compounds would you expect the infrared carbonyl absorption ( stretch) to be at a higher frequency?
    Explain.

CCH

O O

OH OHCCH

Norlutin Enovid

C“O

® ®

H 2 , CH 3 CH 2 SH

(CH 3 CH 2 ) 2 CuLi H 3 O+

CH 3 MgBr H 3 O+

CH 3 CH 2 CCH 2 CH 2 CH 3

OH

CH 2 CH 3

CH 3 CH 2 CCH 2 CH 2 CH 2 CH 3

OH

CH 3 CH 2 CCH 2 CH 2 CH 2 CH 3

O

1. LiAlH 4


2. H 3 O+

O

1. CH 3 MgBr

CH 3

2. H 3 O+

CCH 2 CH 3 +

O

N

H

catalytic

H+

O

1. (CH 3 ) 2 CuLi


2. H 3 O+

CH 3 CCH 2 CH 2 COCH 3

OO

1. excess CH 3 MgBr
   2. H 3 O+

(^13) C NMR
(^1) HNMR
HCl
H 2 O
OCH 3 O
O OCH 2 CH 3
HCl
O

• CH 3 CH 2 OH
  CH 2 CH 2 CH 2 NH 3
  HCl
  H 2 O


• 
  

  Ν O