Leaving Group Conversions - SOCl2 and PBr3 Practice Problems

The following coordinate diagram for the nucleophilic displacement of hydroxide shows that the reaction is unfavorable. Draw a curve demonstrating that the substitution reaction is favorable when tosylate is used.

The following reaction is another method to synthesize haloalkanes using reagents other than PBr₃ and SOCl₂. Propose an arrow-pushing mechanism that rationalizes the production of chloroalkane in the given reaction. (Hint: Begin by reacting dimethyl sulfide and Cl₂. DMS is an excellent nucleophile, whereas Cl₂ is an electrophile.)

Determine the alcohol needed to produce the following bromoalkane using PBr  ₃ as a reagent.

What is the alcohol needed to produce the given bromoalkane using PBr ₃ as a reagent?

Identify the alcohol needed to produce the following bromoalkane using PBr ₃ as a reagent.

The following reaction is another method to synthesize haloalkanes using reagents other than PBr  ₃ and SOCl₂. Propose an arrow-pushing mechanism that rationalizes the production of chloroalkane in the given reaction. (Hint: Begin by reacting dimethyl sulfide and Cl₂. DMS is an excellent nucleophile, whereas Cl ₂ is an electrophile.)

Provide an appropriate reagent that will produce the following stereochemical product of the reaction.

Give the reagent that will produce the stereochemical outcome for the reaction shown below.

Predict the final product of the reaction

Suggest how cis-3-methylcyclopentanol can be converted into the following products.

a. cis-1-chloro-3-methylcyclopentane
b. trans-1-chloro-3-methylcyclopentane

Two products are obtained from the reaction given below.

Propose a suitable mechanism to show why two products are obtained through this reaction. This mechanism should be different from the usual mechanism of the reaction of thionyl chloride with alcohol.

Give balanced chemical equations for the reactions shown below.