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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 the following starting materials into the target compound. You may use any additional reagents you need.

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.

Question: Show how you might synthesize the following compounds, using acetylene and any suitable alkyl halides as your starting materials. If the compound given cannot be synthesized by this method, explain why. (a) hex-1-yne (b) hex-2-yne (c) hex-3-yne (d) 4-methylhex-2-yne (e) 5-methylhex-2-yne (f) cyclodecyne.

When 2,2-dibromo-1-phenylpropane is heated overnight with sodium amide at 150 掳C, the major product (after addition of water) is a different foul-smelling compound of formula C9H8. Propose a structure for this product, and give a mechanism to account for its formation.

Disiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamyl groups. Disiamylborane is prepared by the reaction of BH3. THF with an alkene.

(a) Draw the structural formulas of the reagents and the products in the preparation of disiamylborane.

(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why is Sia3B not formed?
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