Q: Which of the following reactions would convert a primary alcohol to a carboxylic acid?

$$1)\ \text{Na}_2\text{Cr}_2\text{O}_7,\ \text{H}_2\text{SO}_4$$; $$2)\ \text{H}_2\text{O}$$

Question 1

Which of the following compounds would have the furthest downfield shift for a hydrogen in its $$^1H $$NMR spectrum? Consider the effect of electron-withdrawing groups on chemical shift.

Accepted Answer

Benzoic acid ($$C_6H_5COOH)$$

Question 2

Rank the following compounds by the number of unique signals in a spin-decoupled $$^{13}C $$NMR spectrum (from least to most): benzene, toluene, benzoic acid, anisole, and phenol.

Accepted Answer

Benzene \u003c Toluene \u003c Anisole \u003c Phenol \u003c Benzoic acid

Question 3

Which compound would show the highest energy O-H stretch in its IR spectrum?

Accepted Answer

Benzoic acid

Question 4

A compound with molecular formula $$C_3H_8O$$ shows a strong IR absorption near $$3300\ 	ext{cm}^{-1}$$ and a triplet at $$\delta = 1.1$$ ppm in its $$^1H $$NMR. Which compound is it?

Accepted Answer

1-Propanol

Question 5

Which of the following compounds would show the fewest number of $$^{13}C $$NMR signals?

Accepted Answer

Benzene

Question 6

A mass spectrum of an unknown alcohol ($$C_4H_{10}O) $$shows a base peak at $$m/z = 31. $$Which structure is most likely?

Accepted Answer

1-Butanol

Question 7

Which compound would show a singlet at $$\delta = 9-10$$ ppm in its $$^1H $$NMR spectrum?

Accepted Answer

Benzoic acid

Question 8

A compound with molecular formula $$C_3H_6O$$ shows a strong IR absorption at $$1715\ 	ext{cm}^{-1}$$ and a singlet at $$\delta = 2.1$$ ppm in its $$^1H $$NMR. What is the compound?

Accepted Answer

Acetone

Question 9

Which of the following reactions would convert a primary alcohol to a carboxylic acid?

Accepted Answer

$$1)\ 	ext{Na}_2	ext{Cr}_2	ext{O}_7,\ 	ext{H}_2	ext{SO}_4$$; $$2)\ 	ext{H}_2	ext{O}$$

Question 10

Which compound would show a broad IR absorption around $$3300\ 	ext{cm}^{-1}$$ that disappears upon addition of $$D_2O$$?

Accepted Answer

Phenol

Question 11

A $$^1H $$NMR spectrum shows a doublet at $$\delta = 1.2$$ ppm (integrates to 6H) and a septet at $$\delta = 3.0$$ ppm (integrates to 1H). Which compound is this most likely?

Accepted Answer

Isopropyl alcohol

Question 12

Which compound would show a strong IR absorption near $$1700\ 	ext{cm}^{-1}$$ and a singlet at $$\delta = 2.5$$ ppm in its $$^1H $$NMR?

Accepted Answer

Acetophenone

Question 13

Which of the following compounds would show the greatest number of unique $$^1H $$NMR signals?

Accepted Answer

Benzoic acid

Question 14

A compound with molecular formula $$C_4H_{10}O$$ shows a triplet at $$\delta = 0.9$$ ppm and a quartet at $$\delta = 3.5$$ ppm in its $$^1H $$NMR. Which compound is it?

Accepted Answer

Ethoxyethane (diethyl ether)

Question 15

Which of the following compounds would show a strong IR absorption at $$1700\ 	ext{cm}^{-1}$$ and a broad absorption at $$2500-3300\ 	ext{cm}^{-1}$$?

Accepted Answer

Benzoic acid

Question 16

A compound with molecular formula $$C_3H_8O$$ shows a singlet at $$\delta = 1.2$$ ppm and a broad peak at $$\delta = 2.5$$ ppm in its $$^1H $$NMR. Which compound is it?

Accepted Answer

tert-Butanol

Organic Chemistry Spectroscopy and Structure Analysis: Study Guide

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