Chapter 9: Q19P (page 484)
When pent-2-yne reacts with mercuric sulfate in dilute sulfuric acid, the product is a mixture of two ketones. Give the structures of these products, and use mechanisms to show how they are formed.
Short Answer


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Chapter 9: Q19P (page 484)
When pent-2-yne reacts with mercuric sulfate in dilute sulfuric acid, the product is a mixture of two ketones. Give the structures of these products, and use mechanisms to show how they are formed.


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Question:Using hex-1-ene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem)
(a)1,2-dibromohexane
(b)hex-1-yne
(c)2,2-dibromohexane
(d)hex-2-yne
(e)hexan-2-one
(f)hexanal
(g)pentanoic acid
(h)pentanal
(i)undec-6-yn-5-ol
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.
Question: Predict the products formed when reacts with the following compounds.
(a)ethyl bromide
(b)tert-butyl bromide
(c)formaldehyde
(d)cyclohexanone
(e)
(f)cyclohexanol
(g)butan-2-one,
When 2,2-dibromo-1-phenylpropane is heated overnight with sodium amide at 150 °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.
For each compound, give the product(s) expected from (1) HgSO4/H2SO4– catalyzed hydration and (2) hydroboration–oxidation.
(a) hex-1-yne
(b) hex-2-yne
(c) hex-3-yne
(d) cyclodecyne
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