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In the 1H NMR spectrum, which one of the following compounds will show a triplet?

  • A.Ethyl acetate
  • B.Acetone
  • C.Methyl 3,5-dichlorobenzoate
  • D.4-Bromophenol

Answer: A

The key gives (A), ethyl acetate.

In ethyl acetate the OCH2 protons and the CH3 of the ethyl group are the classic pair: the CH3 is split by two neighbouring protons into a triplet (the CH2 is a quartet), while the acetyl CH3 is a singlet. Acetone (B) gives one singlet for its six equivalent protons. 4-Bromophenol (D) has a symmetrical para ring, which gives two doublets, and an OH singlet.

Option (C), methyl 3,5-dichlorobenzoate, is a doubt. Its 4-H has two equivalent meta neighbours, so it appears as a finely split triplet with a coupling of only about 2 Hz, and it is also a triplet by the splitting rule. The key rests on the textbook reading of "triplet" as the vicinal ethyl triplet, so (A) is the keyed answer.

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