Chapter 9: Q16P (page 482)
Predict the major product(s) of the following reactions:
(a) phenylacetylene + 2 HBr
(b) hex-1-yne + 2 HCl
(c) cyclooctyne + 2 HBr
(d) hex-2-yne + 2 HCl
Short Answer
(a)

(b)

(c)

(d)

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Chapter 9: Q16P (page 482)
Predict the major product(s) of the following reactions:
(a) phenylacetylene + 2 HBr
(b) hex-1-yne + 2 HCl
(c) cyclooctyne + 2 HBr
(d) hex-2-yne + 2 HCl
(a)

(b)

(c)

(d)

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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.
Propose a mechanism for the entire reaction of pent-1-yne with 2 moles of HBr. Show why Markovnikov鈥檚 rule should be observed in both the first and second additions of HBr.
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.
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
Question:When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen to give n-butylcyclohexane. Treatment of X with an excess of ozone, followed by dimethyl sulfide and water, gives the following products:

Propose a structure for the unknown compound X. Is there any uncertainty in your structure?
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