Compounds A, B, and C had boiling points near 80°C. Compounds A, B, and C were soluble in water and ether, but their aqueous layers did not change the color of litmus paper. Compounds A, B, and C did not react with acetyl chlo- ride, and they formed a yellow liquid with 2,4-dinitrophenylhydrazine. In their IR spectrum, there was no significant peak between 1600 and 1800; however, there was a large peak around 2250. Compound A reacted with bromine to give a colorless solution; compounds B and C yielded yellowish solutions. Compound B tested positive for a halogen; compounds A and C did not test positive for a halogen. What are the names and structures of these three compounds?

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Compounds A, B, and C had boiling points near 80°C. Compounds A, B, and
C were soluble in water and ether, but their aqueous layers did not change the
color of litmus paper. Compounds A, B, and C did not react with acetyl chlo-
ride, and they formed a yellow liquid with 2,4-dinitrophenylhydrazine. In their
IR spectrum, there was no significant peak between 1600 and 1800; however,
there was a large peak around 2250. Compound A reacted with bromine to
give a colorless solution; compounds B and C yielded yellowish solutions.
Compound B tested positive for a halogen; compounds A and C did not test
positive for a halogen. What are the names and structures of these three
compounds?
Transcribed Image Text:Compounds A, B, and C had boiling points near 80°C. Compounds A, B, and C were soluble in water and ether, but their aqueous layers did not change the color of litmus paper. Compounds A, B, and C did not react with acetyl chlo- ride, and they formed a yellow liquid with 2,4-dinitrophenylhydrazine. In their IR spectrum, there was no significant peak between 1600 and 1800; however, there was a large peak around 2250. Compound A reacted with bromine to give a colorless solution; compounds B and C yielded yellowish solutions. Compound B tested positive for a halogen; compounds A and C did not test positive for a halogen. What are the names and structures of these three compounds?
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