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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The fragrance of (Z)-1-phenylhex-2-en-1-ol resembles that of roses, with a delicate citrus edge. Show how you would synthesize this compound from benzaldehyde (PhCHO) and any other reagents you need.
Question:Show how you would accomplish the following synthetic transformations. Show all intermediates.
(²¹)2,2-»å¾±²ú°ù´Ç³¾´Ç²ú³Ü³Ù²¹²Ô±ð→b³Ü³Ù-1-²â²Ô±ð
(²ú)2,2-»å¾±²ú°ù´Ç³¾´Ç²ú³Ü³Ù²¹²Ô±ð→b³Ü³Ù-2-²â²Ô±ð
(³¦)²ú³Ü³Ù-1-²â²Ô±ð→o³¦³Ù-3-²â²Ô±ð
(d)trans-³ó±ð³æ-2-±ð²Ô±ð→h±ð³æ-2-²â²Ô±ð
(±ð)2,2-»å¾±²ú°ù´Ç³¾´Ç³ó±ð³æ²¹²Ô±ð→h±ð³æ-1-²â²Ô±ð
(´Ú)³¦²â³¦±ô´Ç»å±ð³¦²â²Ô±ð→cis-cyclodecene
(²µ)³¦²â³¦±ô´Ç»å±ð³¦²â²Ô±ð→trans-cyclodecene
(h)hex-1-yne→hexan-2-one, CH3COCH2CH2CH2CH3
(i)hex-1-yne→hexanal, CH3(CH2)4CHO
(j)trans-³ó±ð³æ-2-±ð²Ô±ð→cis-hex-2-ene
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.
Propose a mechanism for the reaction of pent-1-yne with HBr in the presence of peroxides. Show why anti-Markovnikov orientation results.
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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