In the reaction of trans-cinnamaldehyde under the conditions of 2-propanol and gamma-Al2O3, the product yielded is cinnamyl alcohol. When the reaction was first performed the GC and IR showed signals of the formation of a carbocation-like intermediate on the phenyl ring. The 2-propanol used contained high amounts of HCl. How does the high amount of HCl in 2-propanol affect gamma-Al2O? Also, show the intermediate that was formed? The second reaction performed did not contain high amounts of HCl so the product formed was cinnamyl alcohol. Draw the proton NMR spectrum of cinnamyl alcohol.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations
Section11.SE: Something Extra
Problem 78AP: When a primary alcohol is treated with p-toluenesulfonyl chloride at room temperature in the...
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In the reaction of trans-cinnamaldehyde under the conditions of 2-propanol and gamma-Al2O3, the product yielded is cinnamyl alcohol.

When the reaction was first performed the GC and IR showed signals of the formation of a carbocation-like intermediate on the phenyl ring. The 2-propanol used contained high amounts of HCl. How does the high amount of HCl in 2-propanol affect gamma-Al2O? Also, show the intermediate that was formed?

 

The second reaction performed did not contain high amounts of HCl so the product formed was cinnamyl alcohol. Draw the proton NMR spectrum of cinnamyl alcohol.

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