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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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.
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.
For each molecular formula, draw all the isomeric alkynes, and give their IUPAC names. Circle the acetylenic hydrogen of each terminal alkyne.
(a) (three isomers)
(b) (seven isomers)
The boiling points of hex-1-ene (64 °C) and hex-1-yne (71 °C) are sufficiently close that it is difficult to achieve a clean separation by distillation. Show how you might use the acidity of hex-1-yne to remove the last trace of it from a sample of hex-1-ene.
Question:Predict the products of the reaction of but-1-yne with the following reagents.
(a)1 equivalent of HCl
(b)2 equivalents of HCl
(c)excess H2 , Ni
(d) H2 , Pd /BaSO4, quinolone
(e)1 equivalent of Br2
(f)2 equivalents of Br2
(g)cold, dilute KMnO4
(h)warm, concd.KMnO4 , NaOH
(i)Na, liquid ammonia
(j) NaNH2
(k) H2SO4/HgSO4, H2O
(l) Sia2BH, then , H2O2,OH-
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