1  Organic Chemistry I Test 3 Extra Mechanism Practice Problems Page 1: Eliminations to make Alkenes. Page 2+3: Reactions of Alkenes Note: In each of these cases, I am asking you to draw the mechanism for the product shown, even if in some cases there may be other products formed as well. In these problems I’m telling you what type of mechanism is involved; I won’t on a test! J Ch. 7 Elimination Reactions

1.

E2, Small/Normal Base

2.

3.

E2, Bulky Base

4.

E2, Bulky Base using Neutral NEt3

5.

6.

H+-Catalyzed Dehydration

7.

8.

Br NaOCH3

NaOCH3

Br

KO

Br

Br

NEt3

Br NEt3

OH H2SO4

H2SO4

HO

H2SO4

HO

T

  2   Ch. 8 Reactions.

9.

Ionic H-X Addition

10.

11.

H+ catalyzed H2O Addition

12.

13.

X2 addition

   

BrH Br

H Br

Br

PhH+, H2O

Ph

OH

H+, H2O OH

Cl2 Cl

Cl

T

Either the blue or the redmechanism could explain the product with the stereochemistry illustrated.

  3  

14.

X2 addition

15.

X2/H2O addition

16.

17.

H+ catalyzed H2O addition

18.

Br2Ph Ph

H3C

Br

Br

Cl2

H2O

Cl

OH

Br2

H2OH3C

Br

HO

O H2O

H+

OHHO

O CH3 H2O

H+

HO OHCH3

T