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Chapter 11: Q41. (page 451)

Question: Draw the products formed in each reaction and indicate stereochemistry.

a.

b.

c.

d.

Short Answer

Expert verified

Answer

a.

b.

c.

d.

Step by step solution

01

Step-by-Step SolutionStep 1: Nucleophilic substitution reaction

The organic reaction involving the attack of an electron-rich nucleophile at the electrophile to displace a leaving group is known as a nucleophilic substitution reaction.

02

The given nucleophilic substitution reactions a and b

a. As a strong nucleophile, the acetylide anion attacks the electrophilic carbon replacing the chloride anion from the least hindered side. The stereochemistry of the product would be the same as the reactant.


The product formed in reaction a

b. The strong nucleophile would attack the carbon, displacing the leaving group in a bimolecular nucleophilic substitution reaction.


The product formed in reaction b

03

Hydration in reactions c and d

The reaction involving the combination with water molecules is known as hydration.

The intermediates in c. and d. would undergo hydration to give the corresponding enantiomeric mixture of alcohols.

c.

d.

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Most popular questions from this chapter

Question: Draw the enol form of each keto tautomer in parts (a) and (b), and the keto form of each enol tautomer in parts (c) and (d).

a.

b.

c.

d.

Question: Devise a synthesis of the ketone hexan-3-one, CH3CH2COCH2CH2CH3 , from CH3CH2Br as the only organic starting material; that is, all the carbon atoms in hexan-3-one must come from CH3CH2Br . You may use only other needed reagents.

Question: What steps are needed to prepare phenylacetylene, C6H5C≡CH, from each compound:

a.C6H5CH2CHBr2b.C6H5CHBrCH3c.C6H5CH2CH2OH

Question: From what you have learned about enols and the hydration of alkynes, predict what product is formed by the acid-catalyzed hydration of CH3CH2CH2C≡COCH3 . Draw a stepwise mechanism that illustrates how it is formed.

Explain the following result. Although alkenes are generally more reactive than alkynes towards electrophiles, the reaction of with but-2-yne can be stopped after one equivalent of has been added.
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