Heating the following molecule in ethanol gave a major product with molecular formula C;H12 , which when treated with O3 followed by Me2S produced the diketone shown. Br CH3CH,OH 1. O3 C,H12 heat 2. Me,S (i) Deduce the structure of the product with molecular formula C,H12 from the information provided. Write an arrow formalism reaction mechanism to show how

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 33MP
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Heating the following molecule in ethanol gave a major product with molecular formula C,H12 ,
which when treated with O3 followed by Me2S produced the diketone shown.
Br
CH3CH,OH
1. O3
C,H12
heat
2. Me,S
(i)
Deduce the structure of the product with molecular formula C,H12 from the
information provided. Write an arrow formalism reaction mechanism to show how
the compound with molecular formula C,H12 is formed.
(ii)
How would you perform the following transformation to obtain the final product as
the MAJOR product. More than one step is needed. Show all the steps in your
synthesis. Reaction mechanisms are not required.
Br
more than one step
less than four steps
OHC
CHO
Transcribed Image Text:Heating the following molecule in ethanol gave a major product with molecular formula C,H12 , which when treated with O3 followed by Me2S produced the diketone shown. Br CH3CH,OH 1. O3 C,H12 heat 2. Me,S (i) Deduce the structure of the product with molecular formula C,H12 from the information provided. Write an arrow formalism reaction mechanism to show how the compound with molecular formula C,H12 is formed. (ii) How would you perform the following transformation to obtain the final product as the MAJOR product. More than one step is needed. Show all the steps in your synthesis. Reaction mechanisms are not required. Br more than one step less than four steps OHC CHO
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