Exam 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations

Exhibit 11-9 Consider the reaction below to answer the following question(s). -Refer to Exhibit 11-9.Write the complete stepwise mechanism for this reaction.Clearly show the formation of both products.Show all electron flow with arrows and draw all intermediate structures.

For the elimination reaction: Draw the structure present at the point indicated by the asterisk (*) on the following energy diagram.

For the substitution reaction: Draw the structure present at the point indicated by the asterisk (*) on the following energy diagram.

Exhibit 11-4 Consider the pair of reactions below to answer the following question(s). -Refer to Exhibit 11-4.The alkyl bromide starting materials in these reactions are classified as:

Draw the E2 mechanism of the reaction involving the reduction of 2-chloro-butane to 2-butene,in the presence of KOH in ethanol.​

Exhibit 11-6 Consider the reaction below to answer the following question(s). -Refer to Exhibit 11-6.The substrate in the reaction is:

Consider the two energy diagrams below for an S_N2 reaction. A B Which of the following is correct?:

Exhibit 11-6 Consider the reaction below to answer the following question(s). -Refer to Exhibit 11-6.Compound B is the:

For the elimination reaction: Draw the structure present at the point indicated by the asterisk (*) on the following energy diagram

Exhibit 11-9 Consider the reaction below to answer the following question(s). -Refer to Exhibit 11-9.This reaction obeys a rate law of the form:

Consider the two lines shown on the energy diagram below. In an S_N2 reaction,these lines could compare the effect of which of the following solvents?

Consider the two lines shown on the energy diagram below. In an S_N2 reaction,

Exhibit 11-7 To answer the following question(s) consider the data below: Reaction of bromomethane with sodium hydroxide in water forms methanol.If sodium iodide is added to the reaction mixture,the rate of methanol formation is dramatically increased (i.e.sodium iodide is a catalyst). -Refer to Exhibit 11-7.Write a reaction pathway that accounts for the effect of added NaI.

Nucleophilic substitution and elimination reactions often compete with one another.In general,which of the following would enhance the rate of the E2 reaction over the S_N2 reaction?

Exhibit 11-8 Consider the reaction below to answer the following question(s): -Refer to Exhibit 11-8.The mechanism of this reaction is:

Exhibit 11-11 Consider the reaction below to answer the following question(s). -Refer to Exhibit 11-11.As indicated by the carbon numbers,during the course of this reaction the bond between the nitrogen atom and carbon 3 is broken and a bond between the nitrogen atom and carbon 2 is formed.On the structures provided below,draw arrows showing electron flow for the mechanism that accounts for these bonding changes.

Exhibit 11-7 To answer the following question(s) consider the data below: Reaction of bromomethane with sodium hydroxide in water forms methanol.If sodium iodide is added to the reaction mixture,the rate of methanol formation is dramatically increased (i.e.sodium iodide is a catalyst). -Would you expect the same catalytic effect on this reaction if you added NaCl instead? Explain your answer.

Exhibit 11-11 Consider the reaction below to answer the following question(s). -Refer to Exhibit 11-11.If the absolute configuration at carbon 2 in the starting material is R,what is the absolute configuration at carbon 2 in the product?

Exhibit 11-8 Consider the reaction below to answer the following question(s): -Refer to Exhibit 11-8.Draw a Newman projection of the reactive conformation of the starting material.

Exhibit 11-11 Consider the reaction below to answer the following question(s). -Refer to Exhibit 11-11.List all chirality centers in the starting material by number.