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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 structure of compounds A鈥揈 in the following reaction scheme:

Question: What acetylide anion and alkyl halide can be used to prepare each alkyne? Indicate all possibilities when more than one route will work.

a.

b.

c.

What two enols are formed when pent-2-yne is treated with H2O, H2SO4 and , HgSO4? Draw the ketones formed from these enols after tautomerization.

Question: Give the IUPAC name for each alkyne.

a.

b.

c.

d.

e.

f.

Question: N-Chlorosuccinimide (NCS) serves as a source of Cl+in electrophilic addition reactions to alkenes and alkynes. Keeping this in mind, draw a stepwise mechanism for the following addition to buy-2-yne.
See all solutions

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