Chemistry 210
Exam 2 (October 18, 2000)

1. Give the structural formulas for:

trans-3,4-dimethyl-3-hexene

(Z)-3-chloro-4-methyl-3-hexene

(S)-trans-4-methyl-2-hexene

2. Give names and structures for the major product expected from reaction of 2-methylpropene:

H2, Pt  --->

Br2  -->

HBr --> 

HBr (+peroxides) ---> 

H2O, H+  --->

Cl2 + water --->

O3  --->

3. Name the following compounds using IUPAC (or accepted common names) nomenclature:

C=C-C-C-C=C				C=C-C-C-C

C=C-C=C-C=C				C-C=C-C-C-OH

      C-C
      |
C-C-C-C-C-Br				C=C-Cl
  |
  OH

C-C-C-C
    | |
   HO OH

4. Account for the fact that addition of HBr, in the presence of peroxides, takes place faster with 2-ethyl-1-hexene than with 1-octene.

5. Define anti and syn addition. Show the reaction mechanism by which Br₂ (in CHCl₃) adds to propene. Show the bromonium ion reaction intermediate. Explain why this reaction uses the anti or the syn mechanism. If this reaction were performed in water, instead of the organic solvent above, show the structure of the halohydrin product.

6. E2 elimination requires strong base, but E1 does not. Show the mechanism by which either type of elimination occurs.

7. Draw the structure for each product listed below. Then, show the alkene that could be used to produce these products. Show any other reagents necessary for reaction to occur.

t-butyl alcohol

isobutyl bromide

1-chloro-2-methyl-2-butanol

8. Show how hydroboration is used to produce a primay alcohol from propene. Include all required reactants and reaction mechanism.

9. Show the major product of E2 or E1 elimination (dehydrohalogenation or dehydration) of:

C-C-C-C-C-Br					C-C-C-C-C
|
Br
 
  C
  |
C-C-C-C						3-bromo-2-methylpentane
  | |
  C Br

  C
  |
C-C-C-C						4-bromo-2-methylpentane
  | |
  C OH

10. (i) Starting with 2-propanol, show the reaction mechanism for the acid catalyzed formation of a carbocation and formation of propene.  (ii) Show the major alkene product of E1 elimination of 3-methyl-2-butanol and of 3,3-dimethyl-2-butanol.

11. Starting with Cl₂ and butane, show the reaction mechanism for the free radical halogenation reaction. Show structures of the two isomers possible. Which product is the preferred product, and why?

12. Give the definition of an acid and a base using the Lewis definition.

13. Starting with 2-butanol, show the different alkene products you can expect. Which of these products is the major product? Then, show the relative stability of these products.