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5.3: Additional Problems

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Exercise $$\PageIndex{1}$$

Fill in the blanks in the following syntheses.

Exercise $$\PageIndex{2}$$

Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl and nucleophilic substitution at carboxyl.

Exercise $$\PageIndex{3}$$

Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl and nucleophilic substitution at carboxyl.

Exercise $$\PageIndex{4}$$

Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl and nucleophilic substitution at carboxyl (including Wittig and aldol reactions).

Exercise $$\PageIndex{5}$$

Fill in the blanks in the following synthesis involving nucleophilic substitution at carboxyl.

Exercise $$\PageIndex{6}$$

Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, nucleophilic substitution at carboxyl and conjugate addition.

Exercise $$\PageIndex{7}$$

Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, conjugate addition and nucleophilic substitution at carboxyl.

Exercise $$\PageIndex{8}$$

Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, nucleophilic substitution at carboxyl and neutral nucleophilic addition to carbonyl.

Exercise $$\PageIndex{9}$$

Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl/em>, conjugate addition, nucleophilic substitution at carboxyl and transition metal-catalysed coupling.

Exercise $$\PageIndex{10}$$

Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, conjugate addition, nucleophilic substitution at carboxyl and transition metal-catalysed coupling.

Exercise $$\PageIndex{11}$$

Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, conjugate addition, nucleophilic substitution at carboxyl, transition metal-catalysed coupling and neutral nucleophilic addition to carbonyl.

Exercise $$\PageIndex{12}$$

Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, conjugate addition, nucleophilic substitution at carboxyl, transition metal-catalysed coupling and neutral nucleophilic addition to carbonyl.

Exercise $$\PageIndex{13}$$

Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, conjugate addition, nucleophilic substitution at carboxyl, transition metal-catalysed coupling and neutral nucleophilic addition to carbonyl.

Exercise $$\PageIndex{14}$$

Fill in the blanks. Requires knowledge of formation of esters and amides as well as Wittig or Horner-Wadworth-Emmons reactions.

Exercise $$\PageIndex{15}$$

In each case, analyse whether the starting material is a nucleophile or electrophile. Fill in the product in part (c). This question requires knowledge of carbonyl conjugate addition.

These strategies are used in Fukumoto's synthesis of atisine (below).

Answer

Exercise $$\PageIndex{16}$$

Fill in the blanks in the following synthesis of atisine (Keiichiro Fukumoto, Tohoku University). Atisine is a natural product of Aconitum sp., the family of poisonous plants that includes wolfsbane.

Requires knowledge of conjugate addition / Michael reaction, ester reductions, formation of esters and amides, and Wittig or Horner-Wadworth-Emmons reactions.

This page titled 5.3: Additional Problems is shared under a CC BY-NC 3.0 license and was authored, remixed, and/or curated by Chris Schaller via source content that was edited to the style and standards of the LibreTexts platform.

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