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Chapter 24: Q.52. (page 962)

Question: Draw a stepwise mechanism for the following variation of the aldol reaction, often called a nitro aldol reaction.

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Mechanism

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01

Nitro Aldol Reaction

The Henry- reaction or the nitro-aldol reaction is the C-C bond formation reaction which occurs between a nitroalkane and a carbonyl group-containing compound in the presence of a mild base.

02

Mechanism of Nitro Aldol Reaction

The base attacks the acidic hydrogen of the nitroalkane to form a carbanionic center which undergoes resonance stabilization with the nitrogen atom.

As a result, a double bond is generated between the nitrogen and the carbon atom which attacks as a nucleophile on the electron-deficient carbonyl carbon of the carbonyl compound. The product contains an additional C-C between the two starting reactants.

03

Explanation

Stepwise mechanism of the given reaction

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Most popular questions from this chapter

Question: (a) Draw a stepwise mechanism for the reaction of ethyl hexa-2,4-dienoate with diethyl oxalate in the presence of base.

(b) How does your mechanism explain why a new carbon-carbon bond forms on C6?

(c) Why is this reaction an example of a crossed Claisen reaction?

Question: Draw the product of each Robinson annulation from the given starting materials using OHin H2Osolution.

Question:Draw the Claisen product formed from each ester.

Question:What starting materials are needed to prepare each compound using a Michael reaction?

Question: Octinoxate is an unsaturated ester used as an active ingredient in sunscreens.(a) What carbonyl compounds are needed to synthesize this compound using a condensation reaction?(b) Devise a synthesis of octinoxate from the given organic starting materials and any other needed reagents.
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