1. Organic Chemistry, 7e by L. G. Wade, Jr.
Chapter 2 Structure and Properties of Organic Molecules
Christine Hermann
Radford University
Radford, VA
Copyright © 2010 Pearson Education, Inc.

2. 2.1 Which of the following do not describe a sigma bond?
a. Overlap of two s orbitals.
b. Overlap of one s orbital and the end of a p orbital.
c. Side-by-side overlap of p orbitals.
d. Overlap of the end of two p orbitals.

3. 2.1 Answer a. Overlap of two s orbitals.
b. Overlap of one s orbital and the end of a p orbital.
c. Side-by-side overlap of p orbitals.
d. Overlap of the end of two p orbitals.
The side-by-side overlap of p orbitals is a pi bond.

4. 2.2 How many sigma and pi bonds are in a double bond?
a. Two sigma bonds.
b. Two pi bonds.
c. One sigma bond and one pi bond.
d. Two gamma bonds.
e. One sigma bond and one gamma bond.

5. 2.2 Answer a. Two sigma bonds. b. Two pi bonds.
c. One sigma bond and one pi bond.
d. Two gamma bonds.
e. One sigma bond and one gamma bond.
The sigma bond is from the overlap of s orbitals; the pi bond is from the overlap of p orbitals.

6. 2.3 Give the bond angle for CH4.
a. 90o
b o
c. 107o
d o
e. 120o

7. 2.3 Answer
a. 90o
b o
c. 107o
d o
e. 120o
CH4 has a tetrahedral shape, is sp3 hybridized, and has a bond angle of 109.5o.

8. 2.4 Give the hybridization for CH3CN.
a. sp
b. sp2
c. sp3
d. sp4

9. 2.4 Answer
a. sp
b. sp2
c. sp3
d. sp4

10. 2.5 Give the shape for CH3CN. a. Bent. b. Linear. c. Trigonal planar.
d. Trigonal pyramidal.
e. Tetrahedral

11. 2.5 Answer a. Bent. b. Linear. c. Trigonal planar.
d. Trigonal pyramidal.
e. Tetrahedral

12. 2.6 Give the bond angle for CH3CN.
a. 90o
b o
c. 107o
d o
e. 180o

13. 2.6 Answer
a. 90o
b o
c. 107o
d o
e. 180o

14. 2.7 Give the hybridization for the carbon in H2CO.
a. sp
b. sp2
c. sp3
d. sp4

15. 2.7 Answer
a. sp
b. sp2
c. sp3
d. sp4

16. 2.8 Give the hybridization for H2CO.
a. sp
b. sp2
c. sp3
d. sp4

17. 2.8 Answer
a. sp
b. sp2
c. sp3
d. sp4

18. 2.9 Give the shape for H2CO. a. Bent. b. Linear. c. Trigonal planar.
d. Trigonal pyramidal.
e. Tetrahedral.

19. 2.9 Answer a. Bent. b. Linear. c. Trigonal planar.
d. Trigonal pyramidal.
e. Tetrahedral.

20. 2.10 Give the hybridization for the nitrogen in NH4+.
a. sp
b. sp2
c. sp3
d. sp4

21. 2.10 Answer
a. sp
b. sp2
c. sp3
d. sp4

22. 2.11 Identify the type of isomer for CH3OCH3 and CH3CH2OH.
a. Stereoisomer
b. Conformational isomer
c. Constitutional isomer
d. Geometric isomer

23. 2.11 Answer a. Stereoisomer b. Conformational isomer
c. Constitutional isomer
d. Geometric isomer
Constitutional isomers differ in the way the atoms are connected.

24. 2.12 Identify the compound that has London dispersion forces.
a. CH3OCH3
b. CH3CH2OH
c. CH3CH3
d. CH3Cl
e. (CH3)3N

25. 2.12 Answer a. CH3OCH3 b. CH3CH2OH c. CH3CH3 d. CH3Cl e. (CH3)3N
London dispersion forces are forces between nonpolar molecules.

26. 2.13 Identify the compound that has hydrogen bonding.
a. CH3OCH3
b. CH3CH2OH
c. CH3CH3
d. CH3Cl
e. (CH3)3N

27. 2.13 Answer a. CH3OCH3 b. CH3CH2OH c. CH3CH3 d. CH3Cl e. (CH3)3N
A compound must have an H–F, N–H, or O–H bond to have hydrogen bonding.

28. 2.14 Explain why gasoline does not dissolve in water.
a. Both are nonpolar.
b. Both are polar.
c. Gasoline is polar; water is nonpolar.
d. Water is polar; gasoline is nonpolar.

29. 2.14 Answer a. Both are nonpolar. b. Both are polar.
c. Gasoline is polar; water is nonpolar.
d. Water is polar; gasoline is nonpolar.
Gasoline does not dissolve in water because it would have to break up the hydrogen bonding of water.

30. 2.15 Explain why ethanol dissolves in water.
a. Both are nonpolar.
b. Both are polar.
c. Ethanol is polar; water is nonpolar.
d. Water is polar; ethanol is nonpolar.

31. 2.15 Answer a. Both are nonpolar. b. Both are polar.
c. Ethanol is polar; water is nonpolar.
d. Water is polar; ethanol is nonpolar.
Ethanol and water are both polar.

32. 2.16 Identify the general structure of CH3CH2OH.
a. Ether
b. Alcohol
c. Aldehyde
d. Ketone
e. Ester

33. 2.16 Answer a. Ether b. Alcohol c. Aldehyde d. Ketone e. Ester
Alcohols have the general structure of ROH.

34. 2.17 Identify the general structure of CH3CH2COOH.
a. Ester
b. Carboxylic acid
c. Ether
d. Aldehyde
e. Ketone

35. 2.17 Answer a. Ester b. Carboxylic acid c. Ether d. Aldehyde e. Ketone
A carboxylic acid has a general structure of RCOOH.

36. 2.18 Identify the general structure of CH3CH2CH2CHO.
a. Ester
b. Carboxylic acid
c. Ether
d. Aldehyde
e. Ketone

37. 2.18 Answer a. Ester b. Carboxylic acid c. Ether d. Aldehyde e. Ketone
An aldehyde has a general structure of RCHO.

38. 2.19 Identify an amine. a. CH3CH2NHCH3 b. CH3CH2CN c. CH3CH2CONH2
d. CH3CH2CHO
e. CH3COCH2CH3

39. 2.19 Answer a. CH3CH2NHCH3 b. CH3CH2CN c. CH3CH2CONH2 d. CH3CH2CHO
e. CH3COCH2CH3
An amine has a formula of RNH2, R2NH, and R3N.

40. 2.20 Identify a nitrile. a. CH3CH2NHCH3 b. CH3CH2CN c. CH3CH2CONH2
d. CH3CH2CHO
e. CH3COCH2CH3

41. 2.20 Answer a. CH3CH2NHCH3 d. CH3CH2CHO b. CH3CH2CN e. CH3COCH2CH3
c. CH3CH2CONH2
d. CH3CH2CHO
e. CH3COCH2CH3
A nitrile has a formula of RCN.