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Chapter 9: Q21P (page 486)

For each compound, give the product(s) expected from (1) HgSO4/H2SO4鈥� catalyzed hydration and (2) hydroboration鈥搊xidation.

(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

Show how you would convert

(a) oct-3-yne to cis-oct-3-ene.

(b) pent-2-yne to trans-pent-2-ene.

(c) cis-cyclodecene to trans-cyclodecene.

(d) but-1-yne to cis-hex-3-ene.

Predict the product(s) you would expect from the treatment of each compound with (1) dilute, neutral and (2) warm basic , then dilute acid.

(a) hex-1-yne (b) hex-2-yne (c) hex-3-yne

(d) 2-methylhex-3-yne (e) cyclodecyne

When compound Z is treated with ozone, followed by dimethyl sulfide and washing with water, the products are formic acid, 3-oxobutanoic acid, and hexanal.

Propose a structure for compound Z. What uncertainty is there in the structure you have proposed?

Show how hex-1-yne might be converted to

(a) 1,2-dichlorohex-1-ene. (b) 1-bromohex-1-ene.

(c) 2-bromohex-1-ene. (d) 1,1,2,2-tetrabromohexane.

(e) 2-bromohexane. (f) 2,2-dibromohexane.

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)
See all solutions

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