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Explain why and draw the structure of the major product actually formed.

Words: 272
Pages: 1
Subject: Chemistry

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.

  1. Draw the structure, including stereochemistry, of an alkyl chloride that forms

each alkene as the exclusive E2 product.

 

  1. Draw the product(s) formed when treated with excess NaNH2

.

  1. Draw the structure of a dihalide that could be used to prepare the alkene. There

may be more than one possible.

  1. 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.

 

  1. The following reactions do not afford the major product that is given. Explain why

and draw the structure of the major product actually formed.

  1. Draw a detailed, stepwise mechanism for each reaction.

 

  1. 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