Question: ANALYSIS. Five unknown isomeric compounds were found to have the molecular formula C 5 H 1 0 O . Upon Clemmensen reduction, compounds A ,

ANALYSIS. Five unknown isomeric compounds were found to have the molecular formula

C_{5} H_{10} O .

Upon Clemmensen reduction, compounds

A, B,

and

C

all yielded

n -

pentane. These compounds were further subjected to chemical tests to determine their identity. The results of the chemical tests are shown in the table:

Based on the test results, draw the structures of compounds A to E

.

ANALYSIS. Five unknown isomeric compounds were found to have the molecular

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