University of Nairobi Alpha Carbon Organic Chemistry Reactions Questions Please complete all 13 questions in the attached document. For the mechanism quest

University of Nairobi Alpha Carbon Organic Chemistry Reactions Questions Please complete all 13 questions in the attached document. For the mechanism questions please remember to indicate if a step is reversible. 1. i. Draw the enol tautomer for the compound below.
ii. Circle the most stable tautomer.
iii. Explain your reasoning in 20 words or less.
2. Enolate ions are formed using LDA. But, LDA must first be generated by reacting
diisopropylamine with nBuLi. Explain in 20 words or less why chemists do not use nBuLi to
form the enolate ion?
3. An undergraduate student proposed the following synthesis. Explain in 20 words or less
why this route would fail.
4. An undergraduate student proposed the following synthesis using the malonic ester
synthesis as the key step.
i. Would this reaction work.
YES
NO
ii. Explain in 20 words or less why this route would fail
5. The interconversion of keto and enol forms of a carbonyl compound is called
____________________________.
6. i. Circle the major product for the reaction shown below.
ii. Explain your answer in 20 words or less.
7. Complete the reactions below by drawing the missing major product or products,
reactant or starting material. Indicate stereochemistry where appropriate. If the major
products are produced in equal amounts, provide both products.
a.
b.
c.
d.
e.
f.
g.
8. i. Provide a synthesis of the alkene from the indicated starting materials, utilizing a Wittig
reagent as one of your synthetic intermediates. You may use any commercially available reagents
Explain your synthesis in the space provided below.
ii. Now provide an alternative synthesis (from the same starting materials) which utilizes a
Grignard reagent and an elimination. Is this synthesis as efficient as the one that you provided in
part a? If not, what step would be problematic? (Note – Grignard reagents can be synthesized from
alkyl iodides with no problem).
Explain your synthesis in the space provided below
9. Propose a reasonable synthetic route to the given starting material to the target material in the
box. You may use any commercially available reagents, but the starting material is the only allowed
carbon source. You must show how to generate any carbon nucleophiles from stable compounds.
Please show all reagents and intermediates in your synthesis. You do not need to show a
reaction mechanism.
Explain your synthesis in the space provided below.
10. i. Provide a “complete electron pushing” mechanism for the reactions shown below.
Clearly indicate each step of the reaction, including any resonance structures and proton
transfers, and indicate which steps are reversible under the given conditions.
ii. Explain the reaction mechanism that you provided in the space below.
11. i. Provide a “complete electron pushing” mechanism for the reactions shown below.
Clearly indicate each step of the reaction, including any resonance structures and proton
transfers, and indicate which steps are reversible under the given conditions.
ii. Explain the reaction mechanism that you provided in the space below.
12. i. Provide a “complete electron pushing” mechanism for the reactions shown below.
Clearly indicate each step of the reaction, including any resonance structures and proton
transfers, and indicate which steps are reversible under the given conditions.
ii. Explain the reaction mechanism that you provided in the space below.
13. Predict the major elimination product and show a mechanism for its formation.

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