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MCAT Question A Day - 4/6/13 - Answer!

The number of signals in the NMR spectrum of 2-bromopropene is

A.  0
B.  2
C.  3
D.  It cannot be determined.

The correct answer is (C).

a,b, and c indicate the three different kinds of protons. a and (b,c) are clearly chemically inequivalent protons, that is, protons with different environments. b and c, however, are stereochemically inequivalent, and therefore their environments differ as well. Consequently, one would expect three NMR signals to match with three different protons.