Chem 2311. Spring 2012 Homework Problems Chapter 9.

1. For the following compound how many different signals would you see in the proton NMR spectrum? (Assume that you can see them all.)

2. In electron impact mass spectrometry, a beam of high-energy electrons initially dislodges one electron from the compound being studied. This produces a positively charged ion called the ____________________

3. How many chemically distinct 1H NMR signals are there in the following compound?
ClCH2CHCH3 Br

4.

A compound C5H11Cl which exhibits only two singlets in the 1H NMR spectrum must be: B) 1-Chloro-2,2-dimethylpropane; E) 1-Chloro-3-methylbutane C) 1-Chloro-2-methylbutane

A) 1-Chloropentane; D) 3-Chloropentane;

5. In NMR terminology, protons Ha and Hb are said to be:

H Cl Hb Ha

A) Identical;

B) Enantiotopic;

C) Diastereotopic;

D) Homotopic;

E) Mesotopic

6. An organic compound absorbs strongly in the IR at 1687 cm-1. Its 1H NMR spectrum consists of two signals, a singlet at 2.1 ppm and a multiplet centered at 7.1 ppm. Its mass spectrum shows significant peaks at m/z 120, m/z 105 and m/z 77. This information is consistent with which of the following structures?
O O O

II

III

IV

A) I;

B) II;

C) III;

D) IV;

E) V

7. Which proton(s) of the compound below would appear as a septet in the 1H NMR spectrum?
CH3 CH3CH2CH2-O-CH CH3 V IV III II I I

The protons on carbon : A) I;

B) II;

C) III;

D) IV;

E) V

8. How many signals will be recorded in the 13C spectrum of 4-chloro-1-ethylbenzene?

Cl

A) 2;

B) 3;

C) 4;

D) 6;

E) 7

9. The 1H NMR spectrum of which of the compounds below, all of formula C7H12O2, would consist of only two singlets?
O O O O H H O O O O O O

II

III

IV

A) I;

B) II;

C) III;

D) IV;

E) V

10. What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C9H10O2? Relative integration is shown.

5 2 2 1

12

10

8 PPM

CO2H
CHO

CO2H

CO2H

HO2C

1 11. A compound with the molecular formula C8H9BrO gave the following H NMR spectrum: triplet, 1.4; quartet, 3.9; multiplet, 7.0 (4H). There was no evidence of an -OH band in the IR spectrum. A possible structure for the compound is:

Br

Br Br

O Br O

Br

II

III

IV

A) I;

B) II;

C) III;

D) IV;

E) V

12. What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C6H10O2? The 13C-NMR shows characteristic chemical shifts at 22.3, 31.1, 117.3, 157.7, and 171.6 ppm. Relative integration is shown.

1 exchanges w/ D2O 1 1 1

13

12

11

10

7 PPM

CO2H

HO

O O

CO2H

CO2H

13. The mass spectrum of an unknown compound, E, has a molecular ion with m/z = 100. Elucidate the structure of E by scrutinizing its IR, 1H NMR and 13C NMR spectra, shown below.. Show your reasoning.