TCHEM 261 Organic Chemistry Problems

TCHEM 261 Organic Chemistry IIProblem Set H- Elimination Reactions
Name:
Instructions: Complete all problems prior to the deadline. Upload to the Problem Set H
assignment on Canvas. After the key posts, correct your problem set, and upload your
corrections as a second upload to the Problem Set H assignment.
Part 1: Smith Problems
Problems from “Organic Chemistry” 6 ed by Janice Smith.
1. Draw the structures of two different alkyl halides that yield the alkene as the only
product.
Alkyl Halide 1
Alkyl Halide 2
2. Draw all constitutional isomers formed in each elimination reaction. Label the
mechanism as E1 or E2.
E1 or
E2?
3. Taking into account stereochemistry, predict the major E2 product formed. Show
why.
4. Draw the structure, including stereochemistry, of an alkyl chloride that forms
each alkene as the exclusive E2 product.
5.
Draw the product(s) formed when treated with excess NaNH 2
.
6. Draw the structure of a dihalide that could be used to prepare the alkene. There
may be more than one possible.
7. Draw all of the substitution and elimination products formed when the alkyl
halide below is treated with a) CH3OH and b) KOH. Indicate stereochemistry of
products, as well as mechanisms of formation.
8. The following reactions do not afford the major product that is given. Explain why
and draw the structure of the major product actually formed.
9. Draw a detailed, stepwise mechanism for each reaction.
10. Draw a detailed, stepwise mechanism that illustrates how four organic products
are formed in the following reaction:
Product 1:
Product 2:
Product 3:
Product 4:
11. Draw all products formed by treatment of the dibromide (B) with one equivalent
of NaNH2. Label pairs of diastereomers and constitutional isomers.
Part 2: Klein Problems
Klein 10.27-10.38