University of Alabama

CH 231

CHAPTER 5 ALKENES: BONDING, NOMENCLATURE, AND PROPERTIES

MULTIPLE CHOICE

1)What is the approximate value of the CCC bond angle in propene?

a.    90?

b.   109?

c.     120?

d. 180?

2. What is the approximate value of the H?C?H bonds angle in ethene?

a.    90?

b.   109?

c.     120?

d. 180?

3. What is the approximate value of the length of the carbon-carbon bond in ethene?
   1. 121 pm
   2. 134 pm
   3. 142 pm
   4. 154 pm
4. What type of molecular orbital is formed by the overlap of atomic orbitals shown?

4. 1. ? bonding
   2. ? antibonding
   3. ? bonding
   4. ? antibonding
5. What type of molecular orbital is formed by the overlap of atomic orbitals shown?

1. 1. ? bonding
   2. ? antibonding
   3. ? bonding
   4. ? antibonding

6. What type of molecular orbital is formed by the overlap of atomic orbitals shown?

6. 1. ? bonding
   2. ? antibonding
   3. ? bonding
   4. ? antibonding
7. What is the hybridization of carbon atoms labeled i ? iii in the following structure?

1. 1. i = sp; ii = sp; iii = sp
   2. i = sp²; ii = p; iii = sp²
   3. i = sp²; ii = sp; iii = sp²
   4. i = sp²; ii = sp²; iii = sp²

8. What is the hybridization of carbon atoms labeled i ? iii in the following structure?

1. 1. i = sp²; ii = sp²; iii = sp²
   2. i = sp; ii = sp; iii = sp³
   3. i = sp²; ii = sp; iii = sp³
   4. i = sp²; ii = sp²; iii = sp³

9. What is the index of hydrogen deficiency of a compound with a molecular formula of C₅H₁₀?
   1. 0
   2. 1
   3. 2
   4. 3
10. What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₈?
    1. 0
    2. 1
    3. 2
    4. 3

11. What is the index of hydrogen deficiency of a compound with a molecular formula of C₅H₉Br?
    1. 0
    2. 1
    3. 2
    4. 3
12. What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₇Cl?
    1. 0
    2. 1
    3. 2
    4. 3
13. What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₁₅N?
    1. 0
    2. 1
    3. 2
    4. 3
14. What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₁₂N₂?
    1. 0
    2. 1
    3. 2
    4. 3
15. Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 2?
    1. C₅H₈O₂
    2. C₅H₁₀O
    3. C₆H₁₅N
    4. C₅H₁₀Br₂
16. Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 1?
    1. C₅H₈N₂
    2. C₅H₁₁N
    3. C₆H₁₁N
    4. C₅H₁₃NO₂

17. Which of the following compounds has a hydrogen deficiency of 3?

1. 1. only 1
   2. only 2
   3. only 3 and 4
   4. only 1,3 and 4

18. Which of the following compounds does not have a hydrogen deficiency of 5?

1. 1. 1
   2. 2
   3. 3
   4. 4

19. Which of the following does not correspond to a molecular formula of a neutral compound?
    1. C₅H₅Br
    2. C₅H₇Cl₂
    3. C₅H₅Br₃
    4. C₅H₈Cl₄
20. Which of the following does not correspond to a molecular formula of a neutral compound?
    1. C₆H₉NO₂
    2. C₅H₇N₂O₂
    3. C₈H₁₂O₃
    4. C₇H₇N

21. Which of the following does not correspond to a molecular formula of a neutral compound?
    1. C₄H₈BrNO
    2. C₅H₉ClN₂O
    3. C₇H₁₄BrO₃
    4. C₈H₁₄ClN
22. What is the IUPAC name of the following compound?

22. 1. 2-methylenepentane
    2. 2-methyl-1-pentene
    3. 2-vinylpentane
    4. 2-propyl-1-propene
23. What is the IUPAC name of the following compound?

23. 1. 1,3-dimethylhexene
    2. 2,4-dimethyl-2-hexene
    3. 2,4-dimethyl-1-hexene
    4. 3,5-dimethyl-4-hexene
24. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds?
    1. ?CH(CH₃)₂
    2. ?CH₂OCH₃
    3. ?CH₂CH₃
    4. ?CH₂Br
25. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds?
    1. ?COOH
    2. ?Cl
    3. ?CH₂OH
    4. ?CH₃

26. What is the IUPAC name of the following compound?

26. 1. (E)-3-methyl-4-hexene
    2. (Z)-3-methyl-4-hexene
    3. (E)-4-methyl-2-hexene
    4. (Z)-4-methyl-2-hexene
27. What is the IUPAC name of the following compound?

27. 1. (E)-3-methyl-3-pentene
    2. (Z)-3-methyl-3-pentene
    3. (E)-3-methyl-2-pentene
    4. (Z)-3-methyl-2-pentene
28. What is the IUPAC name of the following compound?

28. 1. 2-methyl-4-vinyl-2-pentene
    2. 3,5-dimethyl-1,4-hexadiene
    3. 2,4-dimethyl-3,5-hexadiene
    4. 1,1,3-trimethyl-1,4-pentadiene
29. What is the IUPAC name of the following compound?

1. 1. (Z)-3-ethyl-5-methyl-1,4-heptadiene
   2. (E)-3-ethyl-5-methyl-1,4-heptadiene
   3. (E)-3-methyl-5-vinyl-3-heptene
   4. (Z)-1,3-diethyl-1-methyl-1,4-pentadiene

30. What is the IUPAC name of the following compound?

30. 1. 1,2-dimethylcyclohexene
    2. 2,3-dimethyl-1-cyclohexene
    3. 1,2-dimethyl-2-cyclohexene
    4. 1,6-dimethylcyclohexene
31. What is the IUPAC name of the following compound?

31. 1. 1,3-dimethylcyclopentene
    2. 1,4-dimethylcyclopentene
    3. 2,4-dimethylcyclopentene
    4. 1,3-dimethyl-5-cyclopentene
32. What is the name of the following compound?

1. 1. cis-4-methyl-1-allylcyclohexane
   2. cis-4-allyl-1-methylcyclohexane
   3. trans-4-allyl-1-methylcyclohexane
   4. cis-4-methyl-1-vinylcyclohexane

33. What is the name of the following compound?

33. 1. vinylcyclohexane
    2. allylcyclohexane
    3. methylenecyclohexane
    4. propargylcyclohexane
34. What is the IUPAC name of the following compound?

34. 1. bicyclo[6.2]oct-2-ene
    2. bicyclo[4.4.4]oct-2-ene
    3. bicyclo[2.2.2]-2-octene
    4. bicyclo[2.2]-2-octene
35. What is the IUPAC name of the following compound?

1. 1. bicyclo[5.4.3]-2-octene
   2. bicyclo[5.4.3]-3-octene
   3. bicyclo[3.2.1]-2-octene
   4. 2,6-methyleno-1-cyclooctene

36. Which is the correct assignment of the names of the following compounds?

36. 1. 1 = ethylene; 2 = isobutylene; 3 = isoprene
    2. 1 = acetylene; 2 = isoprene; 3 = isobutylene
    3. 1 = ethylene; 2 = isoprene; 3 = isobutylene
    4. 1 = acetylene; 2 = isobutylene; 3 = isoprene
37. Which is the correct assignment of the names of the following groups?

37. 1. 1 = methylene; 2 = vinyl; 3 = phenyl
    2. 1 = vinyl; 2 = propargyl; 3 = benzyl
    3. 1 = allyl; 2 = vinyl; 3 = benzyl
    4. 1 = vinyl; 2 = allyl; 3 = phenyl
38. Which is the correct assignment of the names of the following groups?

38. 1. 1 = vinyl; 2 = benzyl; 3 = allyl
    2. 1 = allyl; 2 = phenyl; 3 = vinyl
    3. 1 = methylene; 2 = phenyl; 3 = vinyl
    4. 1 = methylene; 2 = benzyl; 3 = allyl
39. How many alkenes have the formula C₅H₁₀?
    1. 4
    2. 5
    3. 6
    4. 7

40. How many constitutional isomeric alkenes are there with the formula C₆H₁₂?
    1. 9
    2. 11
    3. 12
    4. 13
41. How many isomers of 1,6-heptadiene exist?
    1. 1
    2. 2
    3. 3
    4. 4
42. How many isomers of 1,3-heptadiene exist?
    1. 1
    2. 2
    3. 3
    4. 4
43. How many isomers of 2,4-heptadiene exist?
    1. 1
    2. 2
    3. 3
    4. 4
44. How many isomers of 1,3,5-heptatriene exist?
    1. 1
    2. 2
    3. 4
    4. 8
45. What is the smallest trans cycloalkene that is stable at room temperature?
    1. (E) cyclohexene
    2. (E) cycloheptene
    3. (E) cyclooctene
    4. (E) cyclodecene
46. What types of units make up terpenes?
    1. isoprene
    2. propene
    3. vitamin A
    4. pentadiene

47. Which of the following is a terpene?

1. 1. 1
   2. 2
   3. 3
   4. 4

48. Which of the following is not a terpene?

1. 1. 1
   2. 2
   3. 3
   4. 4

49. Which of the following is not true regarding alkenes?
    1. alkenes are non polar
    2. alkenes burn in air to give H₂O and CO₂
    3. alkenes are highly miscible with water
    4. the strongest intermolecular force between alkene molecules is the van der Waals interaction

50. Which of the following compounds is most reactive (least stable)?
    1. (Z)-cycloheptene
    2. (E)-cycloheptene
    3. (Z)-cyclooctene
    4. (E)-cyclooctene

PROBLEM

1. What is the value of the index of hydrogen deficiency of a molecule with the formula C₈H₁₂?

2. What is the value of the index of hydrogen deficiency of a molecule with the formula C₉H₁₀?

3. What is the value of the index of hydrogen deficiency of a molecule with the formula C₇H₁₅N?

4. What is the value of the index of hydrogen deficiency of a molecule with the formula C₈H₁₉N?

5. What is the value of the index of hydrogen deficiency of Ritalin, shown below?

6. What is the value of the index of hydrogen deficiency of aspartame, shown below?

7. What is the IUPAC name of the following compound?

8. What is the IUPAC name of the following compound?

9. What is the IUPAC name of the following compound?

10. What is the IUPAC name of the following compound?

11. What is the IUPAC name of the following compound?

12. What is the IUPAC name of the following compound?

13. What is the IUPAC name of the following compound?

14. What is the IUPAC name of the following compound?

15. What is the IUPAC name of the following compound?