Exam 10: Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Dehydrohalogenation of 2-bromobutane in the presence of a strong base proceeds via which of the following mechanistic pathways?

What reaction mechanism predominates when 1-bromo-1-propylcyclopentane is treated with sodium methoxide in methanol?

Give the major product(s)for the following reaction.

Identify the major organic product for the reaction.

Show the best way to prepare CH₃OCH(CH₃)₂ by an S_N2 reaction.

Which diastereomer of 1-bromo-4-t-butylcyclohexane, the cis or the trans, undergoes elimination more rapidly when treated with sodium ethoxide? Explain your answer.

Give the major product for the following E2 reaction.

Give the best answer for the reaction.

Provide the major organic product of the following reaction.

Draw all likely alkene products in the following reaction and circle the product you expect to predominate.

Draw all likely alkene products in the following reaction and circle the product you expect to predominate.

What is/are the product(s)of the following reaction?

Draw all likely alkene products in the following reaction and circle the product you expect to predominate.

Which of the following alkyl halides forms the most stable carbocation when it undergoes an E1 reaction?

Which of the following halides is least reactive in an E2 reaction with sodium methoxide?

Which of the following compounds undergoes E2 reactions with the fastest rate?

Which of the following compounds is/are the products of the following reaction?

Give the major product for the following reaction.

What is the major product which results when (2R,3S)-2-chloro-3-phenylbutane is treated with sodium methoxide in methanol?

Which sequence of reagents works best to convert 1-bromobutane to hexane?