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Chapter 11: Q42. (page 451)

Question: What reactions are needed to convert alcohol A into either alkyne B or alkyne C?

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01

Step-by-Step SolutionStep 1: Oxidation Reaction

The organic reaction involving the replacement of a hydrogen atom is known as the oxidation reaction.

The primary alpha-substituted butanol undergoes mild oxidation in the presence of oxidizing agents such as pyridinium chlorochromate (PCC), Collin reagent, or silver oxide to give the corresponding aldehyde. This reaction involves homologation.

Formation of product from A

02

Corey-Fuchs Reaction

The conversion of an aldehyde to terminal alkyne using phosphine-dibromo methylene followed by butylated lithium in a quenched medium is known as the Corey-Fuchs reaction.

The aldehyde is treated with a mixture of phosphine-dibromo methylene to give the corresponding dibromo alkene. It undergoes dehalogenation to give an enantiomeric mixture of terminal alkynes.

Formation of products B and C

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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: alkyne gives each compound as the only product after hydroboration鈥搊xidation?

a.

b.

Question:

(a) Draw two different enol tautomers of 2-methylcyclohexanone.

(b) Draw two constitutional isomers that are not tautomers, but contain a C=C and an O-H group.

2-methylcyclohexanone

Question: What alkynes give each of the following ketones as the only product after hydration with H2O,H2SO4andHgSO4?

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b.

c.

d.

Question: Devise a synthesis of the following compound from cyclohexene and acetylene. You may use any other inorganic reagents.
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