Chapter 3 - Alkenes and Alkynes: The Nature of Organic Reactions

Instructions: Classify each reaction below as a(n):

a. addition
b. elimination
c. substitution
d. rearrangement

1.

ANS: C

2.

ANS: D

3.

ANS: A

4. Which of the following is a characteristic of a polar reaction?

a. symmetrical bond making and breaking
b. one electron from each reactant forms the bond
c. involves a neutral species with an unpaired electron
d. are more common that radical reactions
e. all of these
ANS: D

5. In an organic reaction, which of the following is most likely to function as only a nucleophile?
a. BF3
b. (CH3)2CH2NH2
c. Fe2+
d. CH3CH2S

e. both a and c
ANS: D
 Instructions: Identify the functional groups present in each compound below, and predict the
direction of polarity in each.

6. Identify and predict:

mustard gas ClCH2CH2SCH2CH2Cl

ANS:

7. Identify and predict:

amphetamine

ANS:

Instructions: Classify each structure below as a nucleophile or electrophile, and briefly explain your
choice.

8. Classify and explain:

azide

ANS:
Azide ion is a nucleophile because it has a net negative charge (and lots of nonbonding electron
electron pairs!).

9. Classify and explain:

phenol
 ANS: Phenol can be a nucleophile or an electrophile

Instructions: Identify and label the nucleophile and electrophile in each reaction below.

10. Identify and label:

ANS:

11. Identify and label:

ANS:

Instructions: Add curved arrows to the following reaction(s) to indicate the flow of electrons in each.

12. Indicate flow:

ANS:
13. Indicate flow:

ANS:

Instructions: The reaction below is commonly used as a laboratory preparation of cyclohexene. Use
this reaction to answer the following question(s).

14. Refer to instructions. The forward and reverse reactions are classified, respectively, as:
a. addition, elimination
b. elimination, substitution
c. elimination, addition
d. elimination, rearrangement
e. substitution, addition
ANS: C

Instructions: Match each definition to one of the terms below.

a. polarization
b. addition reaction
c. radical reaction
d. electrophile
e. polar reaction
f. substitution
g. nucleophile
h. elimination reaction
15. A reaction that involves a species with an unpaired electron.

ANS: C

16. Another term used for a Lewis acid.

ANS: D
 Instructions: Match each definition to one of the terms below.
a. transition state
b. endergonic reaction
c. activation energy
d. Gibbs free energy change
e. exergonic reaction
f. reaction intermediate
17. A species that lies at an energy maximum during an individual step in a reaction.

ANS: A

18. The energy needed by reactants to reach the transition state.

ANS: C

Instructions: Consider the reaction of 2-bromo-2-methylpropane with water, shown below, to answer
the following question(s).

19. Refer to instructions. This reaction is an example of:

a. a substitution reaction.
b. a rearrangement reaction.
c. an elimination reaction.
d. an addition reaction.
ANS: A

Instructions: In the reaction below:

a) Label the nucleophile (Nu) and the electrophile (E).

b) Draw arrows on the structures showing electron flow in the reaction.

20. Label and indicate flow:

ANS:
 Instructions: Use the reaction energy diagram below to answer the following question(s).

21. The transition state is found at _____ on the diagram.

ANS: B

22. The products are found at _____ on the diagram.

ANS: D

23. The free-energy change for the reaction is indicated at _____ on the diagram.

ANS: C

24. The reactants are found at _____ on the diagram.

ANS: A

25. The following group is a substituent on a molecule. What is an accepted IUPAC name for this group?

a. propenyl
b. allyl
c. vinyl
d. propylene
e. either a or b
ANS: E
26. What is the IUPAC name of the following compound?

a. (E)-3-methylpent-3-ene
b. (Z)-3-methylpent-3-ene
c. (E)-3-methylpent-2-ene
d. (Z)-3-methylpent-2-ene
ANS: D

27. Name this compound.

ANS:
1-ethynyl-2-methylcyclopentane

28. Choose substituents X and Y (listed in order below) for the following compound so as to make a Z
isomer.

a. Br, NHCH3
b. F, CHO
c. I, OCH3
d. COOH, CH2NH2
e. Br, COOH
ANS: B
 Instructions: Draw structures corresponding to each name below.

29. Draw:

(3E)-3,7-dimethylocta-1,3,6-triene

ANS:

30. Draw:

trans-4,4-dimethylpent-2-ene

ANS:

Instructions: Pent-2-ene is an example of a disubstituted alkene. Use this alkene to answer the
following question(s).

31. Refer to instructions. Draw the cis and trans isomers of pent-2-ene and label them.

ANS:

cis trans

32. Refer to instructions. Circle the isomer of pent-2-ene that is most stable.

ANS:
 Instructions: Provide names for each structure below. Be sure to include the cis,trans or E,Z
designations where applicable.

33. Name and designate:

ANS:
trans-2-methylhex-3-ene or (E)-2-methylhex-3-ene

34. Name and designate:

ANS:
3-methylcyclopentene

35. Name and designate:

ANS:
cis-3,3-dimethyl-4-propylocta-1,5-diene or (Z)-3,3-dimethyl-4-propylocta-1,5-diene

36. Rank each set of substituents using the Cahn-Ingold-Prelog sequence rules by numbering the highest
priority substituent 1 and numbering the lowest priority substituent 4. Place the number in the blank
below the substituent.

ANS:
37. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog
system?
a. COOH
b. CHO
c. CH2OH
d. CH3

ANS: A

38. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog
system?
a. NH2
b. NHCH3
c. CH2NH2
d. CH2NHCH3
ANS: B

Instructions: Assign E or Z configurations to each alkene below.

39. Assign:

ANS: Z

40. Assign:

ANS: E

41. The structures below show the stepwise bond making and bond breaking in this reaction. Draw curved
arrows to show the electron flow that has occurred in each step.
 ANS:

42. Predict the product of the following reaction of Prostaglandin H2 by interpreting the flow of electrons
as indicated by the curved arrows.

ANS:

43. Below are all the chemical structures and intermediates involved in a reaction. On the structures
provided, show all electron flow using the arrow formalism for the complete stepwise mechanism.
ANS: