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Chapter 9: Q6P (page 473)

Question: Solved Problem 9-1 showed the synthesis of dec-3-yne by adding the hexyl group first, then the ethyl group. Show the reagents and intermediates involved in the other order of synthesis of dec-3-yne by adding the ethyl group first and the hexyl group last.

Short Answer

Expert verified

Being a strong base and nucleophile, acetylide ion can substitute halide from an alkyl halide, followed by the formation of substituted alkyne. For reaction, the substrate group should be a primary alkyl halide.

Step by step solution

01

Alkylation of acetylide ions 

Being a strong base and nucleophile, acetylide ion can substitute halide from an alkyl halide, followed by the formation of substituted alkyne. For reaction, the substrate group should be a primary alkyl halide.

02

Synthesis of dec-3-yne by adding ethyl and hexyl groups 

The synthesis of dec-3-yne can be done by adding ethyl and hexyl groups to acetylide ions. The addition of ethyl group first with the acetylide ion forms but-3-yne

Then the further addition of hexyl group forms dec-3-yne.

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Most popular questions from this chapter

Question: Give IUPAC names for the following compounds.

a.

b.

c.

d.

e.

f.

(a)Count the elements of unsaturation in cicutoxin, capillin, and panaxytriol.

(b) Draw structural formulas of at least two alkynes of each molecular formula.

(1) C5H8 (2) C8H10 (3) C9H12

The boiling points of hex-1-ene (64 掳C) and hex-1-yne (71 掳C) are sufficiently close that it is difficult to achieve a clean separation by distillation. Show how you might use the acidity of hex-1-yne to remove the last trace of it from a sample of hex-1-ene.

Propose a mechanism for the reaction of pent-1-yne with HBr in the presence of peroxides. Show why anti-Markovnikov orientation results.

Predict the major product(s) of the following reactions:

(a) phenylacetylene + 2 HBr

(b) hex-1-yne + 2 HCl

(c) cyclooctyne + 2 HBr

(d) hex-2-yne + 2 HCl
See all solutions

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