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Question: Many organic compounds contain more than one functional group. Which of the following is both an ald...

Many organic compounds contain more than one functional group. Which of the following is both an aldehyde and an ether?

A

Structure (i): CH3-CH2-O-C(=O)-CH3 This compound contains an ester functional group (-COO-). It is neither an aldehyde nor a simple ether.

B

Structure (ii): CH3-CH2-CH2-C(=O)-CH2-O-CH3 This compound contains a ketone functional group (-C(=O)-) and an ether functional group (-O-CH3). It is not an aldehyde.

C

Structure (iii): This is a cyclopentane ring with two carbonyl groups. One is a ketone within the ring, and the other is an acetyl group (-C(=O)CH3) attached to the ring. It contains two ketone functional groups. It is neither an aldehyde nor an ether.

D

Structure (iv): This compound consists of a five-membered ring containing an oxygen atom, which makes it a cyclic ether. Attached to one of the ring carbons is a -CHO group, which is an aldehyde functional group. Therefore, this compound is both an aldehyde and an ether.

E

Structure (v): CH3-C(=O)-CH2-CH2-O-CH3 This compound contains a ketone functional group (-C(=O)-) and an ether functional group (-O-CH3). It is not an aldehyde.

Answer

Structure (iv) possesses both an aldehyde and an ether functional group.

Explanation

Solution

The question asks to identify the compound that contains both an aldehyde and an ether functional group.

  • Aldehyde functional group: A carbonyl group (C=O) where the carbon is bonded to at least one hydrogen atom and one alkyl or aryl group (R-CHO). R-C(=O)-H
  • Ether functional group: An oxygen atom bonded to two alkyl or aryl groups (R-O-R'). R-O-R'

By examining each option we can conclude that option (iv) is the only compound with both an aldehyde and an ether.