Test Bank for Organic Chemistry with Biological Applications, 3rd Edition

Test Bank for Organic Chemistry with Biological

Applications, 3rd Edition

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Chapter 07 - Alkenes and Alkynes
1. 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
ANSWER: e
POINTS: 1

2. 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
ANSWER: d
POINTS: 1

3. Name this compound.

ANSWER: 1-ethynyl-2-methylcyclopentane
POINTS: 1

4. 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
ANSWER: b

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Chapter 07 - Alkenes and Alkynes
POINTS: 1

5. A molecule has three degrees of unsaturation. In this molecule there would be

a. three rings
b. three double bonds
c. two rings and one double bond
d. one ring and two double bonds
e. any of these
ANSWER: e
POINTS: 1

6. For a compound containing substituents other than hydrogen, the number of hydrogen atoms in the equivalent
hydrocarbon formula is determined by _____ from the number of hydrogen atoms present.
a. subtracting the number of halogens atoms
b. adding two hydrogen atoms for each oxygen
c. subtracting the number nitrogen atoms
d. adding the number of oxygen atoms
ANSWER: d
POINTS: 1

7. A compound with the following molecular formula contains two double bonds. What is the correct subscript for H in
the formula?

C10H?ClN2O
a. 19
b. 22
c. 18
d. 20
e. 21
ANSWER: a
POINTS: 1

8. Calculate the degree of unsaturation in the formula below. Show your calculations.

caffeine, C8H10N4O2
ANSWER: Oxygen does not affect the base formula. One hydrogen is subtracted for each nitrogen, so the base formula
for caffeine is C8H6. A saturated 8 carbon compound should have 18 hydrogens, so the number of degrees of
unsaturation for caffeine is: (18 − 6) / 2 = 6
POINTS: 1

Instructions: Dieldrin, C12H8Cl6O, is a pentacyclic (five-ring) compound formerly used as an insecticide. Use this
information to answer the following question(s).
9. Refer to instructions. Calculate the degree of unsaturation for Dieldrin.
ANSWER: Oxygen does not affect the base formula. One hydrogen is added to the base formula for each halogen, so the
base formula for dieldrin is C12H14. A saturated 12 carbon compound should have 26 hydrogens, so the
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Chapter 07 - Alkenes and Alkynes
number of degrees of unsaturation for dieldrin is:
(26 − 14) / 2 = 6
POINTS: 1

10. Refer to instructions. How many double bonds does dieldrin have?
ANSWER: Dieldrin has 6 degrees of unsaturation and it is pentacyclic. Therefore, dieldrin must have one double bond.
POINTS: 1

Instructions: Draw structures corresponding to each name below.

11. Draw:

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

POINTS: 1

12. Draw:

trans-4,4-dimethylpent-2-ene
ANSWER:

POINTS: 1

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

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

cis trans
POINTS: 1

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

POINTS: 1

Instructions: Provide names for each structure below. Be sure to include the cis,trans or E,Z designations where
applicable.
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Chapter 07 - Alkenes and Alkynes

15. Name and designate:

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

POINTS: 1

16. Name and designate:

ANSWER: 3-methylcyclopentene
POINTS: 1

17. Name and designate:

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

POINTS: 1

18. 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.

ANSWER:

POINTS: 1

19. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system?
a. −COOH
b. −CHO
c. −CH2OH
d. −CH3
ANSWER: a
POINTS: 1

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Chapter 07 - Alkenes and Alkynes
20. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system?
a. −NH2
b. −NHCH3
c. −CH2NH2
d. −CH2NHCH3
ANSWER: b
POINTS: 1

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

21. Assign:

ANSWER: Z
POINTS: 1

22. Assign:

ANSWER: E
POINTS: 1

23. Rank the carbocations below in order of increasing stability (least stable = 1; most stable = 3). Place the number
corresponding to the carbocation's relative stability in the blank below the structure.

ANSWER:

POINTS: 1

24. Alkene chemistry is dominated by what type of reaction?

a. substitution
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Chapter 07 - Alkenes and Alkynes
b. electrophilic addition
c. nucleophilic addition
d. elimination
e. both b and c
ANSWER: b
POINTS: 1

25. Hydride shifts

a. occur to form less highly substituted carbocations.
b. occur by transfer of an H+ between adjacent carbon atoms.
c. are observed only in single step reactions.
d. transfer positive charge to a more highly substituted carbon atom.
ANSWER: d
POINTS: 1

26. Which of the following would have the smallest ΔH°hydrog?

a.
b.

c.

d.

ANSWER: d
POINTS: 1

27. 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.

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Chapter 07 - Alkenes and Alkynes
ANSWER:

POINTS: 1

28. Below are all the chemical structures and intermediates involved in a reaction. Why does the rearrangement that
results in the formation of product B occur?

ANSWER: The 1,2-alkyl shift is the rearrangement of a secondary carbocation to a more stable tertiary carbocation.
POINTS: 1

29. Predict the major organic product(s) in the reaction below. If more than one major organic product is expected, draw
each one.

ANSWER:

POINTS: 1

30. Predict the major organic product(s) in the reaction below. If more than one major organic product is expected, draw
each one. Explain the significance of "35°C" and "ether" shown in the reaction.

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Chapter 07 - Alkenes and Alkynes
ANSWER:

35°C and ether are notes related to the reactions conditions. The reaction is carried out at 35°C and the solvent
is ether.
POINTS: 1

31. The following reaction is carried out in cyclohexane with the application of heat. Write the complete equation for the
reaction below. If more than one major organic product is expected, draw each one.

ANSWER:

POINTS: 1

32. What alkene would you use to prepare the following alkyl halide?

ANSWER: Only one alkene would be possible:

POINTS: 1

33. Using curved arrows, write a mechanism for the following reaction. If carbocations are formed, specify if they are
primary, secondary or tertiary.

ANSWER:

POINTS: 1
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Test Bank for Organic Chemistry with Biological Applications, 3rd Edition

Chapter 07 - Alkenes and Alkynes

Instructions: Match each definition to the term it describes.

a. Hammond Postulate
b. Cahn-Ingold-Prelog Rules
c. Markovnikov's Rule
d. Degrees of Unsaturation

34. Predicts that the more stable carbocation intermediate is formed in electrophilic additions to alkenes.
ANSWER: c
POINTS: 1

35. Predicts that the transition state of an exergonic reaction step structurally resembles the reactant.
ANSWER: a
POINTS: 1

36. Predicts the total number of multiple bonds and rings.

ANSWER: d
POINTS: 1

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