Organic Chemistry II

Problem Set H- Elimination Reactions

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

  1. Draw all constitutional isomers formed in each elimination reaction. Label the mechanism as E1 or E2.

E1 or

E2?

  1. Taking into account stereochemistry, predict the major E2 product formed. Show why.
  2. Draw the structure, including stereochemistry, of an alkyl chloride that forms each alkene as the exclusive E2 product.
  3. Draw the product(s) formed when treated with excess NaNH2
  4. Draw the structure of a dihalide that could be used to prepare the alkene. There may be more than one possible.
  5. 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.
  6. The following reactions do not afford the major product that is given. Explain why and draw the structure of the major product actually formed.
  7. Draw a detailed, stepwise mechanism for each reaction.
  8. 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:

  1. Draw all products formed by treatment of the dibromide (B) with one equivalentof NaNH2. Label pairs of diastereomers and constitutional isomers