Final ExamintonPart 21b Atempt ALL questions (6 questions 12 pages). Please draw

Question

Final ExamintonPart 21b Atempt ALL questions (6 questions 12 pages). Please draw structures neatly. If you hope to obtain partial credit for CHM 4220 Fall 2017 Total Got Lost 1 Consider the compounds below and answer the following questions (3 marks each part) (a) Which compound or compounds cannot undergo any aldol addition or aldol condensation? (b) Which compound or compounds is/are good Nu compounds (enolate components) for crossed aldol reaction? (e) Which compound or compounds can be made efficiently using ethyl acetoacetate and sodium ethoxide? (d) Which compound or compounds will always give mixed products on monoalkylation regardless of the conditions? (e) Which compound or compounds efficiently gives different monoalkylation products on treatment with LDA/CH,l in the cold or with triethylamine and CHyl at high temperature?

Explanation / Answer

A. Compound X, since it doesn't have alpha hydrogens, it is compulsory for Aldol reaction

B. Compound W, since it has two different alpha hydrogens

C. Compound W

D. Compound W, since it has two enolate formation sites.

E. Compound W, since two enolate sites and with LDA, methylation occurs at less substituted enolate since base is bulkier and removes proton from less hindered side while Et3N do on other side.

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