Chapter 9: Q18P (page 482)
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.
Short Answer
(a)

(b)

(c)

(d)

(e)

(f)

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Chapter 9: Q18P (page 482)
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.
(a)

(b)

(c)

(d)

(e)

(f)

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Show how you would convert the following starting materials into the target compound. You may use any additional reagents you need.
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.
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?
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.
The hydroboration–oxidation of internal alkynes produces ketones.
(a) When hydroboration–oxidation 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–oxidation is applied to pent-2-yne, two products are obtained. Show why a mixture of products should be expected with any unsymmetrical internal alkyne.
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