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Identify the following compounds. (Relative integrals are

Chapter 15, Problem 28P

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QUESTION:

Problem 28P

Identify the following compounds. (Relative integrals are given from left to right across the spectrum.)

a. The 1H NMR spectrum of a compound with molecular formula C4H10O2 has two singlets with an area ratio of 2 : 3.

b. The 1H NMR spectrum of a compound with molecular formula C6H10O2 has two singlets with an area ratio of 2 : 3.

c. The 1H NMR spectrum of a compound with molecular formula C8H6O2 has two singlets with an area ratio of 1 : 2.

Questions & Answers

QUESTION:

Problem 28P

Identify the following compounds. (Relative integrals are given from left to right across the spectrum.)

a. The 1H NMR spectrum of a compound with molecular formula C4H10O2 has two singlets with an area ratio of 2 : 3.

b. The 1H NMR spectrum of a compound with molecular formula C6H10O2 has two singlets with an area ratio of 2 : 3.

c. The 1H NMR spectrum of a compound with molecular formula C8H6O2 has two singlets with an area ratio of 1 : 2.

ANSWER:

Solution 28P

(a) The molecular formula () has 10 hydrogens. So, the ratio of  will be . From the area ratio (), the two methyl groups (6 protons) give one signal and the two methylene groups (4 protons) give one signal.

Therefore, the structure of molecular formula () will be:

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