ORGANIC CHEMISTRY 7TH EDITION BY BROWN - TEST BANK

ORGANIC CHEMISTRY 7TH EDITION BY BROWN – TEST BANK

 

Instant Download – Complete Test Bank With Answers

 

 

Sample Questions Are Posted Below

 

CHAPTER 5—ALKENES:  BONDING, NOMENCLATURE, AND PROPERTIES

 

MULTIPLE CHOICE

 

1. What is the approximate value of the C-C-C bond angle in propene?

a.	90°
b.	109°
c.	120°
d.	180°

 

 

ANS:  C

 

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

a.	90°
b.	109°
c.	120°
d.	180°

 

 

ANS:  C

 

3. What is the approximate value of the length of the carbon-carbon bond in ethene?

a.	121 pm
b.	134 pm
c.	142 pm
d.	154 pm

 

 

ANS:  B

 

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

 

 

a.	s bonding
b.	s antibonding
c.	p bonding
d.	p antibonding

 

 

ANS:  C

 

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

 

 

a.	s bonding
b.	s antibonding
c.	p bonding
d.	p antibonding

 

 

ANS:  A

 

 

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

 

 

a.	s bonding
b.	s antibonding
c.	p bonding
d.	p antibonding

 

 

ANS:  A

 

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

 

 

a.	i = sp; ii = sp; iii = sp
b.	i = sp2; ii = p; iii = sp2
c.	i = sp2; ii = sp; iii = sp2
d.	i = sp2; ii = sp2; iii = sp2

 

 

ANS:  C

 

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

 

 

a.	i = sp2; ii = sp2; iii = sp2
b.	i = sp; ii = sp; iii = sp3
c.	i = sp2; ii = sp; iii = sp3
d.	i = sp2; ii = sp2; iii = sp3

 

 

ANS:  D

 

9. What is the index of hydrogen deficiency of a compound with a molecular formula of C₅H₁₀?

a.	0
b.	1
c.	2
d.	3

 

 

ANS:  B

 

10. What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₈?

a.	0
b.	1
c.	2
d.	3

 

 

ANS:  D

 

 

11. What is the index of hydrogen deficiency of a compound with a molecular formula of C₅H₉Br?

a.	0
b.	1
c.	2
d.	3

 

 

ANS:  B

 

12. What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₇Cl?

a.	0
b.	1
c.	2
d.	3

 

 

ANS:  D

 

13. What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₁₅N?

a.	0
b.	1
c.	2
d.	3

 

 

ANS:  A

 

14. What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₁₂N₂?

a.	0
b.	1
c.	2
d.	3

 

 

ANS:  C

 

15. Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 2?

a.	C5H8O2
b.	C5H10O
c.	C6H15N
d.	C5H10Br2

 

 

ANS:  A

 

16. Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 1?

a.	C5H8N2
b.	C5H11N
c.	C6H11N
d.	C5H13NO2

 

 

ANS:  B

 

 

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

 

 

a.	only 1
b.	only 2
c.	only 3 and 4
d.	only 1,3 and 4

 

 

ANS:  D

 

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

 

 

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

 

 

ANS:  D

 

19. Which of the following does not correspond to a molecular formula of a neutral compound?

a.	C5H5Br
b.	C5H7Cl2
c.	C5H5Br3
d.	C5H8Cl4

 

 

ANS:  B

 

20. Which of the following does not correspond to a molecular formula of a neutral compound?

a.	C6H9NO2
b.	C5H7N2O2
c.	C8H12O3
d.	C7H7N

 

 

ANS:  B

 

 

21. Which of the following does not correspond to a molecular formula of a neutral compound?

a.	C4H8BrNO
b.	C5H9ClN2O
c.	C7H14BrO3
d.	C8H14ClN

 

 

ANS:  C

 

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

 

 

a.	2-methylenepentane
b.	2-methyl-1-pentene
c.	2-vinylpentane
d.	2-propyl-1-propene

 

 

ANS:  B

 

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

 

 

a.	1,3-dimethylhexene
b.	2,4-dimethyl-2-hexene
c.	2,4-dimethyl-1-hexene
d.	3,5-dimethyl-4-hexene

 

 

ANS:  B

 

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?

a.	-CH(CH3)2
b.	-CH2OCH3
c.	-CH2CH3
d.	-CH2Br

 

 

ANS:  D

 

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?

a.	-COOH
b.	-Cl
c.	-CH2OH
d.	-CH3

 

 

ANS:  B

 

 

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

 

 

a.	(E)-3-methyl-4-hexene
b.	(Z)-3-methyl-4-hexene
c.	(E)-4-methyl-2-hexene
d.	(Z)-4-methyl-2-hexene

 

 

ANS:  C

 

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

 

 

a.	(E)-3-methyl-3-pentene
b.	(Z)-3-methyl-3-pentene
c.	(E)-3-methyl-2-pentene
d.	(Z)-3-methyl-2-pentene

 

 

ANS:  D

 

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

 

 

a.	2-methyl-4-vinyl-2-pentene
b.	3,5-dimethyl-1,4-hexadiene
c.	2,4-dimethyl-3,5-hexadiene
d.	1,1,3-trimethyl-1,4-pentadiene

 

 

ANS:  B

 

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

 

 

a.	(Z)-3-ethyl-5-methyl-1,4-heptadiene
b.	(E)-3-ethyl-5-methyl-1,4-heptadiene
c.	(E)-3-methyl-5-vinyl-3-heptene
d.	(Z)-1,3-diethyl-1-methyl-1,4-pentadiene

 

 

ANS:  B

 

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

 

 

a.	1,2-dimethylcyclohexene
b.	2,3-dimethyl-1-cyclohexene
c.	1,2-dimethyl-2-cyclohexene
d.	1,6-dimethylcyclohexene

 

 

ANS:  D

 

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

 

 

a.	1,3-dimethylcyclopentene
b.	1,4-dimethylcyclopentene
c.	2,4-dimethylcyclopentene
d.	1,3-dimethyl-5-cyclopentene

 

 

ANS:  B

 

32. What is the name of the following compound?

 

 

a.	cis-4-methyl-1-allylcyclohexane
b.	cis-4-allyl-1-methylcyclohexane
c.	trans-4-allyl-1-methylcyclohexane
d.	cis-4-methyl-1-vinylcyclohexane

 

 

ANS:  D

 

33. What is the name of the following compound?

 

 

 

a.	vinylcyclohexane
b.	allylcyclohexane
c.	methylenecyclohexane
d.	propargylcyclohexane

 

 

ANS:  B

 

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

 

 

a.	bicyclo[6.2]oct-2-ene
b.	bicyclo[4.4.4]oct-2-ene
c.	bicyclo[2.2.2]-2-octene
d.	bicyclo[2.2]-2-octene

 

 

ANS:  C

 

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

 

 

a.	bicyclo[5.4.3]-2-octene
b.	bicyclo[5.4.3]-3-octene
c.	bicyclo[3.2.1]-2-octene
d.	2,6-methyleno-1-cyclooctene

 

 

ANS:  C

 

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

 

 

a.	1 = ethylene; 2 = isobutylene; 3 = isoprene
b.	1 = acetylene; 2 = isoprene; 3 = isobutylene
c.	1 = ethylene; 2 = isoprene; 3 = isobutylene
d.	1 = acetylene; 2 = isobutylene; 3 = isoprene

 

 

ANS:  B

 

 

37. Which is the correct assignment of the names of the following groups?

 

 

a.	1 = methylene; 2 = vinyl; 3 = phenyl
b.	1 = vinyl; 2 = propargyl; 3 = benzyl
c.	1 = allyl; 2 = vinyl; 3 = benzyl
d.	1 = vinyl; 2 = allyl; 3 = phenyl

 

 

ANS:  D

 

38. Which is the correct assignment of the names of the following groups?

 

 

a.	1 = vinyl; 2 = benzyl; 3 = allyl
b.	1 = allyl; 2 = phenyl; 3 = vinyl
c.	1 = methylene; 2 = phenyl; 3 = vinyl
d.	1 = methylene; 2 = benzyl; 3 = allyl

 

 

ANS:  C

 

39. How many alkenes have the formula C₅H₁₀?

a.	4
b.	5
c.	6
d.	7

 

 

ANS:  C

 

40. How many constitutional isomeric alkenes are there with the formula C₆H₁₂?

a.	9
b.	11
c.	12
d.	13

 

 

ANS:  C

 

41. How many isomers of 1,6-heptadiene exist?

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

 

 

ANS:  A

 

 

42. How many isomers of 1,3-heptadiene exist?

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

 

 

ANS:  B

 

43. How many isomers of 2,4-heptadiene exist?

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

 

 

ANS:  D

 

44. How many isomers of 1,3,5-heptatriene exist?

a.	1
b.	2
c.	4
d.	8

 

 

ANS:  C

 

45. What is the smallest trans cycloalkene that is stable at room temperature?

a.	(E)-cyclohexene
b.	(E)-cycloheptene
c.	(E)-cyclooctene
d.	(E)-cyclodecene

 

 

ANS:  C

 

46. What types of units make up terpenes?

a.	isoprene
b.	propene
c.	vitamin A
d.	pentadiene

 

 

ANS:  A

 

47. Which of the following is a terpene?

 

 

 

 

 

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

 

 

ANS:  B

 

48. Which of the following is not a terpene?

 

 

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

 

 

ANS:  A

 

49. Which of the following is not true regarding alkenes?

a.	Alkenes are non polar.
b.	Alkenes burn in air to give H2O and CO2.
c.	Alkenes are highly miscible with water.
d.	The strongest intermolecular force between alkene molecules is the van der Waals interaction.

 

 

ANS:  C

 

50. Which of the following compounds is most reactive (least stable)?

a.	(Z)-cycloheptene
b.	(E)-cycloheptene
c.	(Z)-cyclooctene
d.	(E)-cyclooctene

 

 

ANS:  B

 

TRUE/FALSE

 

1. 2-methyl-2-hexene can exhibit cis/trans isomerism.

 

ANS:  F

 

 

2. The structure for 2,3-dimethyl-2-pentene is shown below.

 

ANS:  F

 

3. The following compound contains an allyl group.

 

ANS:  F

 

4. The following compound contains a carbon-carbon double bond with Z stereochemistry.

 

ANS:  T

 

5. The following molecular formula could represent an alkene.

C₂₇H₅₆

 

ANS:  F

 

6. In the carbon-carbon bond of an alkene,  a p bond is considerably weaker than a s bond.

 

ANS:  T

 

7. The presence of both rings and pi bonds contribute to the index of hydrogen deficiency in a compound.

 

ANS:  T

 

8. In the calculation of the index of hydrogen deficiency,  when the elements of Group 6 are found in a formula no correction to the number of hydrogen atoms is needed.

 

ANS:  T

 

9. (3E)-3,7-dimethyl-1,3,6-octatriene can be represented by either of the following two formulas.

 

 

ANS:  T

 

 

10. Consider the following two structures.

 

 

 

The structure on the left represents the more stable form of this compound.

 

ANS:  F

 

11. The following could be named as either trans-2-methylhex-3-ene or (Z)-2-methylhex-3-ene .

 

 

ANS:  F

 

COMPLETION

 

1. The following substance contains ______ terpene units.

 

ANS:  Two               2

 

Consider the compounds named below.   Use the letter of the substance to answer the following questions.   Some letters may be used more than once.  Some questions may have more than one correct answer.  In the latter case,  only one letter need be given.

 

1. propene
2. 1-butene
3. 2-butene
4. 1-pentene
5. 2-pentene

 

2. The compound with the lowest boiling point is represented by the letter ______.

 

ANS:  a

 

3. A compound likely to be a liquid at room temperature is represented by the letter ______.

 

ANS:  d                    e

 

4. A compound that can exhibit cis–trans isomerism is represented by the letter ______.

 

ANS:  e

 

 

5. A compound with the following molecular formula contains two double bonds. The correct subscript for H in the formula is ________.

 

C₁₀H_?ClN₂O

 

ANS:  19                  nineteen

 

6. Using the EZ system,  the following would designated as the ____isomer.

 

 

ANS:  E                    E

 

PROBLEM

 

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

 

ANS:  three

 

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

 

ANS:  five

 

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

 

ANS:  one

 

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

 

ANS:  zero

 

 

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

 

ANS:  six

 

 

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

 

ANS:  seven

 

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

 

ANS:  (E)-3-methyl-2-hexene

 

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

 

ANS:  (Z)-5-methyl-2-hexene

 

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

 

ANS:  (Z)-3-chloro-4-methyl-2-pentene

 

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

 

ANS:  (E)-4-chloro-3-methyl-2-pentene

 

 

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

 

ANS:  1,6-dimethylcyclohexene

 

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

 

ANS:  1,4-dimethylcyclohexene

 

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

 

ANS:  3,4-dimethylcyclopentene

 

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

 

ANS:  3,5-dimethylcyclopentene

 

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

 

ANS:  (2Z,5Z)-2,5-octadiene

 

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

 

ANS:  (2E,4Z)-2,4-octadiene

 

17. Provide the bond-line structure of (2E,5E)-2,5-octadiene.

 

ANS:

 

18. Provide the bond-line structure of (2Z,6E)-octa-2,6-diene.

 

ANS:

 

19. Provide the bond-line structure of (Z)-4,5-dichloro-2-pentene.

 

ANS:

 

20. Provide the bond-line structure of (E)-3-chloro-3-hexene.

 

ANS: