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Chapter 9: Q21P (page 486)

For each compound, give the product(s) expected from (1) HgSO4/H2SO4– catalyzed hydration and (2) hydroboration–oxidation.

(a) hex-1-yne

(b) hex-2-yne

(c) hex-3-yne

(d) cyclodecyne

Short Answer

Expert verified

Alkyne is hydrated using the Kucherov reaction using the reagent dilute sulphuric acid and special reagent mercury sulfate HgSO4/H2SO4 .

Hydration of alkyne follows Markovnikov's rule, and intermediate enol is formed during the reaction.

Step by step solution

01

Hydration of Alkyne

Alkyne is hydrated using the Kucherov reaction using the reagent dilute sulphuric acid and special reagent mercury sulfate HgSO4/H2SO4 .

Hydration of alkyne follows Markovnikov's rule, and intermediate enol is formed during the reaction.

02

Products from HgSO4/H2SO4 - catalyzed hydration

(a) HgSO4/H2SO4catalyzed reaction of hex-1-yne from hex-2-one product.


(b) HgSO4/H2SO4catalyzed reaction of hex-2-yne from a mixture of two products hex-2-one and hex-3-one.

(c) HgSO4/H2SO4catalyzed reaction of hex-3-yne from hex-3-one product

(d) HgSO4/H2SO4catalyzed reaction of cyclodecyne forms cyclodecaone product.

03

Products from the hydroboration oxidation reaction

(a) Hydroboration oxidation reaction of hex-1-yne from hexanone product.

The hydroboration oxidation reaction of (a)

(b) Hydroboration oxidation reaction of hex-2-yne from a mixture of two products hex-2-one and hex-3-one.

(c) Hydroboration oxidation reaction of hex-3-yne from hex-3-one product.

(d) Hydroboration oxidation reaction of cyclodecyne forms cyclodecaone product

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Most popular questions from this chapter

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

Propose a mechanism for the entire reaction of pent-1-yne with 2 moles of HBr. Show why Markovnikov’s rule should be observed in both the first and second additions of HBr.

Question:Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)

(a)cis-cyclooctene

(b)cyclooctane

(c)trans-1,2-dibromocyclooctane

(d)cyclooctanone

(e)1,1-dibromocyclooctane

(f)3-bromocyclooctene

(g)cyclooctane-1,2-dione

(h)

(i)

Oxidative cleavages can help to determine the positions of the triple bonds in alkynes.

(a) An unknown alkyne undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid. Propose a structure for the alkyne.

(b) An unknown alkyne undergoes oxidative cleavage to give the following triacid plus one equivalent of propionic acid. Propose a structure for the alkyne.

What reaction would acetylene likely to undergo if it were kept at 1500 oC for too long?
See all solutions

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