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Chapter 17: Q.41. (page 641)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

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Step by step solution

01

Reaction mechanism

The reaction mechanism gives an account of the various steps taking place in a particular reaction. The electron shift is denoted by arrows in a reaction mechanism.

02

Reaction with NaH

Sodium hydride (NaH) is utilized as a base in several organic reactions. Several condensation reactions like Stobbe condensation and Claisen condensation make use of NaH as a reagent.

03

Stepwise mechanism of the given reaction

Formation of the first compound involves two steps. In the first step, carbanion intermediate is formed. Abstraction of proton happens in the second step leading to the product formation.

The formed carbanion gets subjected to delocalization at different carbon atoms to give rise to the second and the third compound.

Stepwise mechanism of the reaction

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Most popular questions from this chapter

Question: Use the inscribed polygon method to show the pattern of molecular orbitals in cyclooctatetraene.

a. Label the MOs as bonding, antibonding, or nonbonding.

b. Indicate the arrangement of electrons in these orbitals for cyclooctatetraene, and explain why cyclooctatetraene is not aromatic.

c. Treatment of cyclooctatetraene with potassium forms a dianion. How many蟺electrons does this dianion contain?

d. How are the 蟺electrons in this dianion arranged in the molecular orbitals?

e. Classify the dianion of cyclooctatetraene as aromatic, antiaromatic, or not aromatic, and explain why this is so.

Question: Which compound in each pair is the stronger acid?

What orbitals are used to form the labeled C-Cbonds in the following molecule? Of the labeled bonds, which is the shortest?

Question: Early structural studies on benzene had to explain the following experimental evidence. When benzene was treated with Br2(plus a Lewis acid), a single substitution product of molecular formula C6H5Brwas formed. When this product was treated with another equivalent of Br2, three different compounds of molecular formularole="math" localid="1648727281591" C6H4Br2 were formed.

  1. Explain why a single Kekule structure is consistent with the first result, but does not explain the second result.
  2. Then explain why a resonance description of benzene is consistent with the results of both reactions.

Question: You have a sample of a compound of molecular formula C11H15NO2, which has a benzene ring substituted by two groups, (CH3)2N-and -CO2CH2CH3 , and exhibits the given C13 NMR. What disubstituted benzene isomer corresponds to these C13 data?
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