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Chapter 9: Q35 E (page 286)

Question: Identify the reagents a–c in the following scheme:

Short Answer

Expert verified

The reagents a, b, c can be given as:

Reagent a - NaNH2, NH3and CH3CH2Br

Reagent b- H2and Lindlar’s catalyst

Reagent c- CH2I2 and Zn(Cu)

Step by step solution

01

Reagents used for the conversion of alkynes to other compounds

Alkynes can be reduced to cis alkenes by treating them with hydrogen in the presence of Lindlar’s catalyst. They can also be converted to higher alkynes by treating them withNaNH2 , ammonia and the required alkyl halide.

02

 Identifying the reagents for the following conversion

The first reactant, 3-methylbut-1-yne reacts with reagent a, NaNH2, NH3 and CH3CH2Br and gets converted to 2-methylhex-3-yne. This product reacts with reagent b, H2 and Lindlar’s catalyst to form the product (Z)-2-methylhex-3-ene. This further reacts with reagent c, CH2I2 and Zn(Cu) to form the product (1S,2S)-1-ethyl-2-isopropylcyclopropane.

The overall reaction can be given as:

Reagents involved in the reaction

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Most popular questions from this chapter

Which of the following bases could be used to deprotonate 1-butyne?

d)

Each of the following syntheses requires more than one step. How

would you carry them out?

(a)

(b)

A cumulene is a compound with three adjacent double bonds. Draw an orbital picture of a cumulene. What kind of hybridization do the two central carbon atoms have? What is the geometric relationship of the substituents on one end to the substituents on the other end? What kind of isomerism is possible? Make a model to help see the answer.

R2C=C=C=CR2

A cumulene

Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.

a.CH3CH2CH2C≡CH

The oral contraceptive agent Mestranol is synthesized using a carbonyl addition reaction like that shown in Problem 9-50. Draw the structure of the ketone needed.
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