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Chapter 20: Q78 (page 816)

Identify X and Y, two of the intermediates in a synthesis of the antidepressant venlafaxine (trade name Effexor), in the following reaction scheme. Write a mechanism for the formation of X from W.

Short Answer

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Step by step solution

01

Robinson annulation

The combination reaction of the Michael reaction and the Aldol reaction named the Robinson annulation is useful in generating a structure containing a six-membered ring.

02

Mechanism of Robinson annulation reaction

The carbonyl compound containing a more acidic -hydrogen is attacked by the base and thus reacts with the other carbonyl compound to form an enolate. The enolate then undergoes reaction.

The obtained product undergoes tautomerization and hence an intramolecular aldol reaction to form a six-membered ring.

03

Mechanism of the given reaction

The mechanism of the given reaction is given hereunder:

Stepwise mechanism of the given reaction

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Most popular questions from this chapter

Draw a stepwise mechanism for the following reaction.

Draw a stepwise mechanism for the following reaction. (Hint: Conjugate addition can occur with heteroatoms as well as carbon nucleophiles.)

Draw the product formed when the $α, β$ -unsaturated ketone A is treated with each reagent.

$(a) {NaBH}_{4}, {CH}_{3} OH (b) H_{2}, (1 equiv), Pd - C (c) H_{2}, (excess), Pd - C (d) [1] {CH}_{3} Li; [2] H_{2} O (e) [1] {CH}_{3} {CH}_{2} MgBr; [2] H_{2} O (f) [1] {({CH}_{2} = {CH}_{2})}_{2} CuLi; [2] H_{2} O$

An unknown compound A (molecular formula $C_{7} H_{14} O$ ) was treated with ${NaBH}_{4} in {CH}_{3} OH$ to form compound B (molecular formula $C_{7} H_{16} O$ ). Compound A has a strong absorption in its IR spectrum at 1716 ${cm}^{- 1}$ . Compound B has a strong absorption in its IR spectrum at 3600–3200 ${cm}^{- 1}$ . The ${}^{1}H$ NMR spectra of A and B are given. What are the structures of A and B?

Draw the products of each reduction reaction.

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