4. A student was asked to prepare an alkene X in high yield using any alcohol as starting material CH3 CH;-C- -CH=CH, CH3 He chose 3, 3-dimethylbutan-2-ol (XI) and carried out a dehydration reaction. He was however horrified to note that the only alkene obtained was XII. CH3 OH CH3 CH, -C=c-CH, conc. H,SO4 CH CH-CH3 heat CH3 CH3 XI XII i) Explain what went wrong here, and why X could not be formed from 3, 3-dimethylbutan-2-ol. Use structures to help support your answer. ii) Give an equation to show a much better method for preparing X in high yield.

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4. A student was asked to prepare an alkene X in high yield using any alcohol as starting material
CH3
CH,-C
-CH=CH,
CH3
X
He chose 3, 3-dimethylbutan-2-ol (XI) and carried out a dehydration reaction. He was however
horrified to note that the only alkene obtained was XII.
CH3
OH
CH3
CH;-C=C-CH3
conc. H,SO4
CH-CH3
heat
CH3
CH3
XI
XII
i) Explain what went wrong here, and why X could not be formed from 3, 3-dimethylbutan-2-ol. Use
structures to help support your answer.
ii) Give an equation to show a much better method for preparing X in high yield.
5. Analyze the following structure and write one combination for Grignard reagent and a carbonyl that
would give rise to it.
CH,-CH,-OH
Transcribed Image Text:4. A student was asked to prepare an alkene X in high yield using any alcohol as starting material CH3 CH,-C -CH=CH, CH3 X He chose 3, 3-dimethylbutan-2-ol (XI) and carried out a dehydration reaction. He was however horrified to note that the only alkene obtained was XII. CH3 OH CH3 CH;-C=C-CH3 conc. H,SO4 CH-CH3 heat CH3 CH3 XI XII i) Explain what went wrong here, and why X could not be formed from 3, 3-dimethylbutan-2-ol. Use structures to help support your answer. ii) Give an equation to show a much better method for preparing X in high yield. 5. Analyze the following structure and write one combination for Grignard reagent and a carbonyl that would give rise to it. CH,-CH,-OH
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