Takehome Quiz 8 Name:(Last) (First) 1. Draw the structure of the base LDA below: 2. Complete the following reactions by filling in the missing Reactant, Reagents, or MAJOR Product. a. b. O O 1. LDA / THF 2. Br c. d. e. f. g. h. i. 3. Circle the structure that IS a resonance form of the structure shown below. a.

Takehome Quiz 8 Name:(Last) (First) 1. Draw the structure of the base LDA below: 2. Complete the following reactions by filling in the missing Reactant, Reagents, or MAJOR Product. a. b. O O 1. LDA / THF 2. Br c. d. e. f. g. h. i. 3. Circle the structure that IS a resonance form of the structure shown below. a. 4. The reaction of 3,5-dimethylheptanoic acid with ethyl propyl amine in the presence of dicyclohexylcarbodiimide leads to the formation of an amide product. Provide a detailed mechanism to account for the formation of the amide product. 5. Provide a detailed mechanism for how 2-pentylhexanoic acid could be synthesized using the malonic ester synthesis. 6. Provide a detailed mechanism for how 3-isobutyl-2-hexanone could be synthesized using acetoacetic acid synthesis. 7. Identify (draw the structure) the missing reagent, reactant, or major product required to complete the following transformations. Fill in your answers in the corresponding blanks on the following page. (2 Points Each) NEXT PAGE IS ANSWER SHEET O OH O Br CuLi 2 HO HCl / 875oC O O 1. DIBAL, toluene 2. H3O+ OH (DCC) N N HN N A C D B F I H G E J MgBr Problem 6 Answer sheet A. _____________________________ B. ___________________________ C. _____________________________ D. ___________________________ E. ______________________________ F. ___________________________ G. ______________________________ H. ___________________________ I. _______________________________ J. ___________________________ 8. Propose a Mechanism to account for the formation of the product shown. Hint Combination of Michael Addition and Aldol condensation.

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