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Chapter 9: Q35 E (page 286)

Question: Identify the reagents a鈥揷 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鈥檚 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鈥檚 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鈥檚 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

The sex attractant given off by the common housefly is an alkene named muscalure. Propose a synthesis of muscalure starting from acetylene and any alkyl halides needed. What is the IUPAC name for muscalure?

Muscalure

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

would you carry them out?

(a)

(b)

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

a.CH3CH2CH2C鈮�CH

Using any alkyne needed, how would you prepare the following alkenes?

(c) 3-Methyl-1-pentene

Occasionally, a chemist might need to invert the stereochemistry of an alkene鈥攖hat is, to convert a cis alkene to a trans alkene, or vice versa. There is no one-step method for doing an alkene inversion, but the transformation can be carried out by combining several reactions in the proper sequence. How would you carry out the following reactions?

(a)tran-5-decene鈫�?cis-5-decene

(b)cis-5-decene鈫�?trans-5-decene
See all solutions

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