Q: Given the molecular formula $$\mathrm{C$$_{10}$$H_{13}NO_3$}$$, how do you calculate the elements of unsaturation (EU)?

C_{10} \text{ max H} = $$C_{10}H$$_{22} \text{ and MF 'becomes' } $$C_{10}H$$_{12}

Question 1

Given the molecular formula $$\mathrm{C$$_{10}$$H_{13}NO_3$}$$, how do you calculate the elements of unsaturation (EU)?

Accepted Answer

C_{10} 	ext{ max H} = $$C_{10}H$$_{22} 	ext{ and MF 'becomes' } $$C_{10}H$$_{12}

Question 2

Why is the trans, trans isomer of [10]-annulene NOT aromatic?

Accepted Answer

It is not planar

Question 3

Why will the Williamson ether synthesis shown below NOT work? (Reacting 2-bromopropane with sodium methoxide)

Accepted Answer

The reaction will not work because the major product will be an E2 reaction

Question 4

Addition of the proton from HCl to which carbon of 2,3-dimethyl-1-butene would give the best carbocation?

Accepted Answer

C2

Question 5

Which of the following compounds represents a meta-substituted benzoic acid?

Accepted Answer

A benzene ring with CO_2H at position 1 and $$OCH_3 at $$position 3

Question 6

Which of the following is NOT an ether?

Accepted Answer

$$\mathrm{CH_3CH_2OH}$$

Question 7

Which of the following molecules and ions are aromatic?

Accepted Answer

Y only

Question 8

The IR spectrum below shows a strong absorption at $$1747\ \mathrm{cm}^{-1}. $$Which functional group is most likely present?

Accepted Answer

Ester

Question 9

Which of the following is an allylic carbocation?

Accepted Answer

A carbocation adjacent to a double bond

Question 10

Which of the heterocyclic aromatic compounds shown below is the weakest base?

Accepted Answer

Pyrimidine

Question 11

Which of the following reactions will yield a chiral epoxide (oxirane)?

Accepted Answer

Epoxidation of cis-2-butene with $$\mathrm{RCO_3H}$$

Question 12

Based on its predicted IR spectrum, a compound with a strong, broad absorption around $$3300\ \mathrm{cm}^{-1}$$ and a sharp absorption near $$1700\ \mathrm{cm}^{-1}$$ would most likely be confused with what other functional group?

Accepted Answer

Carboxylic acid

Question 13

Which of the following statements is FALSE concerning the addition reaction shown below? (1,2- and 1,4-addition to a conjugated diene)

Accepted Answer

Structure I is a monosubstituted alkene.

Question 14

What is the IUPAC name of the compound below? (A six-membered ring with two methyl groups at positions 2 and 6, and a nitrogen atom in the ring)

Accepted Answer

2,6-dimethylpyridine

Question 15

Which of the following molecules is least polar?

Accepted Answer

$$\mathrm{CH_3OCH_3}$$

Question 16

Calculate the elements of unsaturation (EU) for a molecule with molecular formula $$\mathrm{C_6H_{12}}.$$

Accepted Answer

$$\mathrm{EU} = 1$$

Question 17

Which IR spectrum (1–4) corresponds to a carboxylic acid?

Accepted Answer

Spectrum 3

Question 18

Which IR spectrum (1–4) corresponds to an alcohol?

Accepted Answer

Spectrum 1

Question 19

Which IR spectrum (1–4) corresponds to a nitrile?

Accepted Answer

Spectrum 4

Question 20

Which IR spectrum (1–4) corresponds to a ketone?

Accepted Answer

Spectrum 2

Organic Chemistry Exam Study Guide: IR Spectra, Aromaticity, and Reaction Mechanisms

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