[PDF] [PDF] General Organic Chemistry Questions

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[PDF] General Organic Chemistry Questions

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Organic Chemistry Questions

The Covalent Bond

1. The hybridization of the central carbon in CH

3

CN and the bond angle CCN are

a. sp 2 , 180°. b. sp, 180°. c. sp 2 , 120°. d. sp 3 , 109°.

2. Which of the following statements about an sp hybridized carbon is FALSE?

a. It is divalent. b. It forms bonds that are linear. c. It has two p orbitals. d. It always forms triple bonds to carbon.

3. Which molecule has the largest dipole moment?

a. HCl b. CCl 4 c. H 2 S d. CO 2

4. What are the hybridizations of carbons 1 and 2 respectively in the following structure?

a. sp 3 and sp 2 b. sp 2 and sp 3 c. sp 3 and sp d. sp 2 and sp 2

5. What are the hybridizations of atoms 1 and 2 respectively in the following structure?

a. sp 3 and sp 2 b. sp 2 and sp 3 c. sp 3 and sp d. sp 2 and sp 2

6. Identify the orbital hybridization at the two indicated carbons in the molecule below.

a. C 1 : sp; C 2 : sp b. C 1 : sp 2 ; C 2 : sp 2 c. C 1 : sp; C 2 : sp 2 d. C 1 : sp 2 ; C 2 : sp

7. How many total resonance structures can be drawn for the following anion (include

those without separation of charge)? a. 1 b. 2 c. 3 d. 4

8. How many resonance structures can be drawn for the following molecule?

a. 1 b. 4 c. 3 d. 2

9. The correct geometry around oxygen in CH

3 OCH 3 is a. linear. b. bent. c. tetrahedral. d. trigonal planar

10. Determine the relationship between the two molecules shown.

a. constitutional isomers b. enantiomers c. diastereomers d. identical molecules

11. What is the correct name for this molecule?

a. (2R,3R)-2-bromo-3-chlorobutane b. (2S,3R)-2-bromo-3-chlorobutane c. (2S,3S)-2-bromo-3-chlorobutane d. (2R,3S)-2-bromo-3-chlorobutane

12. What is the specific rotation 20[Į ]

D of the following molecule? a. +4.42 o b. +0.442 o c. +44.2 o d. - 44.2 o

13. Which of the following physical properties differ for each of a pair of enantiomers?

a. solubility in ethanol b. direction of rotation of plane-polarized light c. boiling point and melting point d. index of refraction

14. Determine the double bond stereochemistry (E or Z) for the following molecules.

a. A: E; B: E b. A: Z; B: Z c. A: E; B: Z d. A: Z; B: E

15. Determine the double bond stereochemistry (E or Z) for the following molecules.

a. A: E; B: E b. A: Z; B: Z c. A: E; B: Z d. A: Z; B: E

Molecular Structure and Spectra

1. A strong signal at 1700 cm

-1 in an IR spectrum indicates the presence of a(n) a. alcohol b. ether c. carbonyl d. amine

2. A strong signal at 3400 cm

-1 in an IR spectrum indicates the presence of a(n) a. alcohol b. ether c. carbonyl d. amine

3. Deduce the structure of an unknown compound with molecular formula C

5 H 12

O using

information given by its infrared spectrum.

Intensity (peak): Frequency (cm

-1 m 3300 m 2900 m 2800 m 1465 m 1450 m 1375 a. b. c. d.

4. Deduce the structure of an unknown compound with molecular formula C

9 H 10

O using

information given by its infrared spectrum.

Intensity (peak): Frequency (cm

-1 s 3100 m 2900 m 2800 s 1710 m-w 1600 m-w 1475 m 1465 m 1450 m 1375 a. b. c. d.

5. Deduce the structure of an unknown compound with molecular formula C

5 H 8

O using

information given by its infrared spectrum.

Intensity (peak): Frequency (cm

-1 m 3100 m 2800 s 1705 m-w 1640 m 1450 m 1375 a. b. c. d.

6. Which of the following compounds a-d has an IR absorption at 3300 cm

-1 a. a b. b c. c d. d

7. When an external magnetic field is applied, what happens to the protons in a sample?

a. All protons align with the field. b. All protons align opposite to the field. c. Some protons align with the field and some align opposite to it. d. All protons assume a random orientation

8. Which of the following compounds has the MOST deshielded protons?

a. CH 3 Cl b. CH 3 I c. CH 3 Br d. CH 4

9. Arrange the following compounds in order of decreasing chemical shift for the

underlined hydrogens (largest value first, smallest value last). CH 3 CH 2 CH 3 CH 3 OCH 2 CH 3 Cl 2 CHCH 2 CH 3 ClCH 2 CH 2 CH 3 a b c d a. b > c > a > d b. b > c > d > a c. c > b > a > d d. c > b > d > a

10. An unknown molecule A has 4 signals in the

1

H NMR spectrum. Which of the

following corresponds to molecule A? a. b. c. d.

11. Deduce the structure of an unknown compound using the following

1 H NMR spectrum, mass spectroscopy data, and IR spectrum. 1

H NMR spectrum:

1.30 (triplet, 6H)

4.29 (quartet, 4H)

7.4-7.9 (multiplet, 4H)

Mass Spectrum:

m/e: Intensity: (as % of base peak)

222 10%

177 38%

149 100%

IR Spectrum:

Intensity (peak): Frequency (cm

-1 s 3100 m 2900 m 2800 s 1740 m-w 1600 m-w 1475 m 1465 m 1450 m 1375 s 1300-1000 a. b. c. d.

12. A compound of formula C

5 H 12 gives 1 signal in the 1

H NMR and 2 signals in the

13 C

NMR. The compound is

a. pentane. b. 2-methylbutane. c. 2,2-dimethylpropane. d. Cannot tell without more information.

13. How many methyl peaks would you expect to observe in the

1

H NMR spectrum of

cis-1,4-dimethylcyclohexane? a. 1 b. 2 c. 3 d. 4

14. An unknown compound A has the molecular formula C

4 H 8 O 2 . Based on the following 1 H NMR spectrum, what is the structure of compound A? a. b. c. d.

15. The

1 H NMR spectrum of a compound is shown below. What is the structure of the compound? a. b. c. d.

16. How many absorption bands will appear in the

13

C NMR spectrum for the following

compound? a. 4 b. 6 c. 7 d. 8

17. How many absorption bands will appear in the

13

C NMR spectrum for the following

compound? a. 5 b. 7 c. 8 d. 9

18. Not only the molecular ion peak, but all peaks in the mass spectrum of chlorobenzene

are accompanied by a smaller peak one mass unit higher. This peak is due to which of the following? a. capture of an H atom b. presence of a 13 C c. presence of a 36
Cl d. capture of a proton

19. What is the exact mass (in atomic mass units: C, 12.0000; H, 1.0078; N, 14.0031; O,

15.9949) of the molecular ion of a compound with molecular formula C

3 H 8 O? a. 60.0000 b. 60.0573 c. 60.0624 d. 59.9949

Separations and Purifications

1. Which of the following may be separated by ordinary physical methods?

a. a pair of identical molecules b. a pair of enantiomers c. a pair of diastereomers d. a pair of identical atoms

2. Which of the following may be separated by ordinary physical methods?

a. (R)-3-bromo-1-butene and (S)-3-bromo-1-butene b. cis-2-bromo-2-butene and trans-2-bromo-2-butene c. (2R,3S)-1,2-dibromobutane and (2S,3R)-1,2-dibromobutanequotesdbs_dbs11.pdfusesText_17