Chapter 12 Problem Set 1.

Predict and name the major products (assume same moles of halide as diene): + HBr + HBr + Br2 + Br2 -78oC
Br

4-bromo-2-hexene 2-bromo-3-hexene
Br Br

60oC -15oC 40oC

4,5-dibromo-2-hexene
Br Br

2,5-dibromo-3-hexene
Br

2. Show the mechanisms of both the 1,2-addition path and the 1,4-addition path: + HBr H
Br H H

Br
H

Br

Br Br H H

3. Show the thermodynamic and kinetic products of the reaction and label each type of product (assume same number of moles of halide as diene): HCl
Cl

Cl

kinetic product 1,2-addition

thermodynamic product 1,4-addition

Chapter 12 Problem Set Which molecules have or can haves-cis configuration?:

Show the products (show stereochemistry where appropriate):

O OCH 3 H

+
OCH 3 O O OCH 3 H

COOCH 3 COOCH 3

COOCH 3 COOCH 3

H3CO O O OCH 3

H COOCH 3 H

O OCH 3 COOCH 3 OCH 3 O O H O O H3CO H O COOCH 3

+
H3CO O

Chapter 12 Problem Set Determine the necessary diene and dieneophile needed to make the following products:

OCH 3 O

OCH 3 O

COOCH 3 COOCH 3

O O O O O O COOCH 3 OCH 3 O O OCH 3 O COOCH 3 O

+
O O

OCH 3 O

OCH 3 O

COOCH 3 COOCH 3

OCH 3 O

OCH 3 O

COOCH 3 COOCH 3