EXAM 3

Please numerically rank the compounds/reactions in each of the following categories (1 = best compound or fastest reaction for each criterion.) Briefly rationalize each answer.

Using the reaction of below to illustrate, provide an orbital-based justification as to why water is strong enough to deprotonate the sp3 C-H bond in an E1 reaction. A graphical depiction of your answer must be provided to receive full credit.

Please numerically rank the compounds/reactions in each of the following categories (1 = best compound or fastest reaction for each criterion.) Briefly rationalize each answer. a) Base performance in E2 reaction:

Please numerically rank the compounds/reactions in each of the following categories (1 = best compound or fastest reaction for each criterion.) Briefly rationalize each answer. Nucleophiles in an SN2 reaction in CH3OH:

Please numerically rank the compounds/reactions in each of the following categories (1 = best compound or fastest reaction for each criterion.) Briefly rationalize each answer. Alkyl halide performance in an SN1 reaction:

Shown below is the bromination of 3-methylhexane. Notice that a racemic mixture of products is isolated. Please comment on this and provide a graphical molecular orbital picture of the reactive intermediate that shows the origin of the stereochemical outcome of the reaction. (hint: hybridization of a radical?)

Please identify the major product of the following radical halogenation reaction and calculate the anticipated percent yield that would be obtained. Keep in mind the following selectivity factors for bromination: 3° : 2° : 1° = 1600 : 82 : 1.

Please use curved arrows (fish-hooks) to draw a complete mechanism for the reaction in part (a). Clearly label the steps involved in radical mechanisms. Be sure to include all lone pairs, formal charges, and resonance structures in your answer!

Please provide a reasonable arrow-pushing mechanism for each of the following reactions. Note: be sure to show all resonance structures (if any), lone pairs, and formal charges!

For each of the following reactions, please identify the type of reaction favored (either SN1, SN2, E1, E2) and draw the major product(s). Note: be sure to clearly show product stereochemistry!

For each of the following reactions, please identify the type of reaction favored (either SN1, SN2, E1, E2) and draw the major product(s). Note: be sure to clearly show product stereochemistry!

For each of the following reactions, please identify the type of reaction favored (either SN1, SN2, E1, E2) and draw the major product(s). Note: be sure to clearly show product stereochemistry!

For each of the following reactions, please identify the type of reaction favored (either SN1, SN2, E1, E2) and draw the major product(s). Note: be sure to clearly show product stereochemistry!

For each of the following reactions, please identify the type of reaction favored (either SN1, SN2, E1, E2) and draw the major product(s). Note: be sure to clearly show product stereochemistry!

For each of the following reactions, please identify the type of reaction favored (either SN1, SN2, E1, E2) and draw the major product(s). Note: be sure to clearly show product stereochemistry!

Propose rational syntheses for the following molecule from the starting material given. You may use any additional reactants/reagents that your synthetic route may require.

Propose rational syntheses for the following molecule from the starting material given. You may use any additional reactants/reagents that your synthetic route may require.

Propose rational syntheses for the following molecule from the starting material given. You may use any additional reactants/reagents that your synthetic route may require.

Provide the major product of the following reactions

Provide the major product of the following reactions

Provide the major product of the following reactions

Draw the mechanism for the following reaction:

Provide the major product of the following reactions

Provide the major product of the following reactions