Chapter 9: Q42P (page 495)
Using any necessary inorganic reagents, show how you would convert acetylene and isobutylbromide to
(a)meso-2,7-dimethyloctane-4,5-diol,(CH3)2CHCH2CH(OH)CH(OH)CH2CH(CH3)2 .
(b) (± ) -2,7-dimethyloctane-4,5-diol
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Chapter 9: Q42P (page 495)
Using any necessary inorganic reagents, show how you would convert acetylene and isobutylbromide to
(a)meso-2,7-dimethyloctane-4,5-diol,(CH3)2CHCH2CH(OH)CH(OH)CH2CH(CH3)2 .
(b) (± ) -2,7-dimethyloctane-4,5-diol
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Give common names for the following compounds.
(a) (b)
(c) 3-methyloct-4-yne (d)
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
Show how you would convert the following starting materials into the target compound. You may use any additional reagents you need.
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.
In the addition of just 1 mole of bromine to 1 mole of hept-1-yne, should the hept-1-yne be added to a bromine solution or should the bromine be added to the hept-1-yne? Explain your answer.
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