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Chapter 9: Q9-10 Pb (page 278)

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

b.(CH3)2CHC鈮�CCH2CH3

Short Answer

Expert verified

Answer

b.CH32CHC鈮�CH+CH3CH2Br鈫�CH32CHC鈮�CCH2CH3

Step by step solution

01

Alkylation

Migration of the alkyl group from one molecule to another via carbanion or carbocation formation

02

Alkylation of acetylide ion

Acetylide ion is a strong nucleophile that reacts with the electrophile like alkyl halide that replaces the halide and forms alkyne. Hence new C-C bond is formed, and the old C-Br bond is broken.

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Most popular questions from this chapter

How would you carry out the following transformation? More than one

step is needed.

Question: Identify the reagents a鈥揷 in the following scheme:

What products would you obtain by hydration of the following alkynes?

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

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
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