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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

The hydroboration鈥搊xidation of internal alkynes produces ketones.

(a) When hydroboration鈥搊xidation is applied to but-2-yne, a single pure product is obtained. Determine the structure of this product, and show the intermediates in its formation.

(b) When hydroboration鈥搊xidation is applied to pent-2-yne, two products are obtained. Show why a mixture of products should be expected with any unsymmetrical internal alkyne.

Question: Predict the products formed when CH3CH2-C鈮�C:Na+ reacts with the following compounds.

(a)ethyl bromide

(b)tert-butyl bromide

(c)formaldehyde

(d)cyclohexanone

(e)CH3CH2CH2CHO

(f)cyclohexanol

(g)butan-2-one,CH3CH2COCH3

Question: Give IUPAC names for the following compounds.

a.

b.

c.

d.

e.

f.

Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.

(a) 3-methylnon-4-yn-3-ol (鈥�3-ol鈥� means there is an OH group on C3.)

(b) cis-1-ethyl-2-methylcyclopropane

(c)

(d) meso-hexane-3,4-diol

Show how you would convert the following starting materials into the target compound. You may use any additional reagents you need.
See all solutions

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