Free Printable Organic Chemistry Final Exam

1.

What is the approximate bond angle around the indicated carbons (left C, right C)?

a)

$105\degree,109.5\degree$

b)

$107\degree,180\degree$

c)

$109.5\degree,120\degree$

d)

$120\degree,109.5\degree$

e)

$180\degree,120\degree$

2.

What is the hybridization around the indicated carbons (left C, right C)?

a)

sp3, sp2

b)

sp2, sp3

c)

sp, sp2

d)

sp3, sp3

e)

sp, sp3

3.

What type of reaction is the following?

a)

Addition

b)

Elimination

c)

Substitution

d)

Rearrangment

e)

Combustion

4.

How many hydrogens are on the following molecule?

a)

5

b)

6

c)

7

d)

8

e)

None of the above

5.

Which is not a correct Lewis dot structure?

a)

b)

c)

d)

e)

More than one of the above is not correct.

6.

Select the set of formal charges that fit the indicated carbon and oxygen (N first, O second).

a)

+1, +1

b)

-1, 0

c)

0, 0

d)

0, +1

e)

None of the above

7.

Choose the proper symbol to fill in the box for this reaction.

a)

b)

c)

d)

8.

Name of the following molecule.

a)

isopropyl bromide

b)

isobutyl bromide

c)

sec-butyl bromide

d)

tert-butyl bromide

e)

None of the above.

9.

Name the following molecule.

a)

6-ethyl-4-methylheptane

b)

2-ethyl-2,4-dimethylheptane

c)

2,4-dimethyl-2-ethylheptane

d)

2-ethyl-3,5-dimethylhexane

e)

None of the above.

10.

Name the following molecule.

a)

1 -bromo-3 -chloro-6-butylcycloheptane

b)

1 -chloro-3-bromo-5-butylcycloheptane

c)

C. 3 -bromo-5-butyl- I -chlorocycloheptane

d)

3 -bromo-I-butyl-5-chlorocycloheptane

e)

1-chloro-3-bromo-5-butylcycloheptane

11.

What are the functional groups labeled in the following structure?

a)

I= alcohol, II = nitrile, III = acid, IV= alkyne

b)

I: ketone, II: amine, III: acid, IV: alkyne

c)

I: ketone, II : imine, III: ether, IV: alkene

d)

I = aldehyde, II: amine, III: ester, IV: alkene

e)

I: ketone, II : amine, III: ester, IV: alkene

12.

Which of the following is NOT a constitutional isomer of "1.".

a)

b)

c)

13.

Which of the following would have the lowest boiling point?

a)

$CH_3CHO$

b)

$CH_3CH_2CH_3$

c)

$\left(CH_3\right)_2NH$

d)

$CH_3OCH_3$

e)

All above molecules have the same boiling point.

14.

Rank the conformations of butane, sighting down the C2-C3 bond, from most stable to the least stable conformation.

a)

eclipsed>gauche>anti

b)

anti>gauche>eclipsed

c)

gauche>anti>eclipsed

d)

anti>eclipsed>gauche

e)

eclipsed>anti>gauche

15.

(Listed in order) How many primary, secondary, tertiary, and quaternary carbons are in the following molecule?

a)

5, 8, 5, 1

b)

3, 8, 5, 3

c)

5, 8, 3, 3

d)

3, 10, 5, 1

e)

None of the above

16.

Which is the most stable, structure of 1-isopropyl-4-methylcyclohexane.

a)

b)

c)

d)

17.

How many resonance structures, including the one given, can be drawn for the given structure?

a)

2

b)

3

c)

4

d)

5

e)

None of the above.

18.

Which of the following is bicyclo [3.2.1] octane?

a)

b)

c)

d)

e)

19.

which compound is different from the others?

a)

b)

c)

d)

e)

All are the same.

20.

In the lowest energy conformation of the compound below, how many substituents (side groups) are axial? (Hint: draw chair conformations for this molecule)

a)

0

b)

1

c)

2

d)

3

21.

Which of the following compounds will undergo an E2 reaction most readily?

a)

$\left(CH_3\right)_2Cl$

b)

$\left(CH_3\right)_2CHI$

c)

$\left(CH_3\right)_2CHCH_2CH_2CH_2I$

d)

$\left(CH_3\right)_2CHCH_2CH_2CH_2Cl$

e)

$\left(CH_3\right)_2CCH_2I$

22.

$S_N2$ reactions involving chiral reactivity centers usually proceed with:

a)

inversion of configuration

b)

slightly more inversion than retention.

c)

slightly more retention then inversion.

d)

retention of configuration.

e)

equal amounts of inversion and retention of configuration.

23.

$S_N1$ reactions involving chiral reactivity centers usually proceed with:

a)

inversion of configuration

b)

slightly more inversion than retention.

c)

slightly more retention then inversion.

d)

retention of configuration.

e)

equal amounts of inversion and retention of configuration.

24.

What type of solvent would lead to a faster reaction rate for an $S_N1$ reaction?

a)

nonpolar

b)

polar aprotic

c)

polar protic

d)

nonpolar protic

e)

solvent is not important in determining rate.

25.

Which of the following substrates has the fastest rate for an $S_N2$ reaction?

a)

b)

c)

d)

26.

Which of the following substrates has the fastest rate for an $S_N1$ reaction?

a)

b)

c)

d)

27.

which of the following is a strong base but a weak nucleophile?

a)

b)

c)

d)

28.

which of the following is both a strong base and a strong nucleophile?

a)

b)

c)

d)

29.

What product(s) would be expected from the following reaction?

a)

I only

b)

II only

c)

III only

d)

I and II

e)

II and III

30.

What elimination product is formed in the following reaction?

a)

A

b)

B

31.

What elimination product is formed in the following reaction?

a)

A

b)

B

32.

what is the name product if an elimination reaction gives the more substituted double bond?

a)

Hofmann

b)

Markovnikov

c)

Gilman

d)

Zaitsev

e)

Grignard

33.

which mechanism is the following reaction most likely to follow?

a)

SN1

b)

SN2

c)

E1

d)

E2

e)

More than one of the above.

34.

which mechanism is the following reaction most likely to follow?

a)

SN1

b)

SN2

c)

E1

d)

E2

e)

More than one of the above.

35.

The solvent in this reaction is:

a)

nonpolar aprotic

b)

polar aprotic

c)

polar protic

d)

nonpolar protic

36.

Which peak is most likely to be the base peak in the mass spec for the following?

a)

72

b)

57

c)

54

d)

43

e)

29

37.

Which peak is most likely to be the base peak in the mass spec for the following?

a)

72

b)

57

c)

54

d)

43

e)

29

38.

The following IR is representative of which molecular formula?

a)

C5H12

b)

C5H10

c)

C5H8

d)

C5H12O

e)

C5H13N

39.

The following IR is representative of which functional group?

a)

aldehyde

b)

alkene

c)

alkyne

d)

alcohol

e)

amine

40.

How many different peaks should be present in the $C^{13}$ NMR spectrum of the following molecule?

a)

4

b)

5

c)

6

d)

7

e)

None of the above.

41.

How many different peaks should be present in the $C^{13}$ NMR spectrum of the following molecule?

a)

4

b)

5

c)

6

d)

7

e)

None of the above.

42.

How many different peaks should be present in the $C^{13}$ NMR spectrum of the following molecule?

a)

4

b)

5

c)

6

d)

7

e)

None of the above.

43.

Which of the following reagents substitute a Br in place of OH of a secondary alcohol?

a)

HBr

b)

NBS

c)

$Br_2$

d)

$PBr_3$

e)

All of the above are correct.

44.

In an SN2 reaction, for which set of solvents is the first listed the best solvent?

a)

DMSO and HMPA

b)

CH3OH and H2O

c)

CH3OH and CH3CH2OH

d)

CH3CN and CH3OH

45.

Which is the best answer for the product(s) of the following substitution reaction?

a)

b)

c)

racemic mixture of a and b

d)

mixture of the product a with the minor product b

46.

Consider the elimination reaction, the product(s) of the reaction is(are):

a)

$CH_3CH_2CH_2CH=CHCH_3$

b)

$CH_3CH_2CH_2CH_2CH=CH_2$

c)

am equimolar mixture of a and b.

d)

a mixture of the major product a with minor product b

e)

a mixture of the major product b with minor product a

47.

which of the following reagants gives the following reaction?

a)

HBr

b)

NBS

c)

Br2

d)

PBr3

e)

All of the above are correct

48.

in the following SN2 reaction which reactant acts as the nucleophile?

a)

A

b)

B

c)

C

d)

D

49.

Which one of the following molecules have a dipole moment?

a)

$CCl_4$

b)

$CH_4$

c)

$CO_2$

d)

$CH_3CH_2OH$

e)

More than one of the above

50.

What type of reaction is the following?

a)

Combustion

b)

Propagation

c)

Elimination

d)

Substitution

e)

Rearrangment

51.

How many degrees of unsaturation does C₆H₅NO₂ have?

a)

2

b)

7

c)

9

d)

10

e)

None of the above

52.

Which set(s) of the following are NOT diastereomers?

a)

1 compared to 2

b)

1 compared to 3

c)

2 compared to 3

d)

2 compared to 4

e)

All of the above answers (a-d) are diastereomers.

53.

Assign the R or S configuration to any chiral centers.

a)

R

b)

S

c)

Cannot be determined

54.

How many total arrows would be used in all steps for the mechanism for the following reaction?

a)

3

b)

4

c)

5

d)

6

e)

More than 6

55.

Which of these carbocation is least likely to undergo a single hydride shift to produce a more stable carbocation?

a)

b)

c)

56.

Classify this reaction

a)

Addition

b)

Elimination

c)

Substitution

d)

Rearrangment

57.

Classify this reaction

a)

Addition

b)

Substitution

c)

Elimination

d)

Rearrangment

58.

How many different monochlorinated products are expected in the free radical chlorination for the following reactants...

a)

1

b)

2

c)

3

d)

4

e)

5

59.

a)

b)

c)

d)

e)

None of the above

60.

Which of the following reagents gives butane from 2-butyne?

a)

$H_2\ ,$ Pd/C

b)

$Li$ / $NH_3$

c)

$H_2\ ,\$ Lindlar's Catalyst

d)

$NaNH_2$

e)

More than one of the above

61.

Which of the following reactions would produce butanone from 1-butyne?

a)

$O_3$

b)

$KMnO_4$

c)

$BH_3,\ THEN\ H_2O_2$

d)

$H_2SO_4\ ,\ H_2O\ ,\ HgSO_4$

e)

None of the above

62.

Use the following table to answer.

The given reaction is in the answer boxes, choose the correct letter it corresponds to.

a)

b)

a

c)

b

d)

c

e)

d

63.

In the hydrohalogenation of an alkene, the alkene is the:

a)

Nucleophile

b)

Electrophile

64.

What is the major product of the following reaction?

a)

b)

c)

d)

e)

More than one correct answer.

83.

In the reaction of an acetylide ion with bromoethane- the acetylide ion is the:

a)

Electrophile

b)

Nucleophile

84.

Alkenes may be hydrated by the hydroboration/oxidation procedure shown.

The intermediate formed in the first step of this reaction is:

a)

b)

c)

d)

85.

When 0₃ reacts with 3,4-dimethyl-1-hexyne. we say that the reaction occurs with:

a)

Cleavage and Partial oxidation

b)

Cleavage. and complete oxidation

c)

Epoxldatlon

d)

Diol formation

e)

None of the above

86.

How many chiral centers are in:

a)

1

b)

3

c)

5

d)

7

e)

None of the above

87.

Which is the proper order for carbocation stability (from lowest to highest stability)?

a)

1,2,3

b)

2,3,1

c)

3,1,2

d)

3,2,1

e)

2,1,3

88.

Which splitting pattern would NOT be present in the NMR of the following molecule?

a)

Singlet

b)

Doublet

c)

Triplet

d)

Quartet

e)

All of the above are present

89.

Name the following molecule.

a)

3,6-dimethyl-1,4-cyclohexadiene

b)

1,4-dimethyl-3,6-cyclohexadiene

c)

1,4-dimethyl-1,4-cyclohexadiene

d)

2,5-dimethyl-1,3-cyclohexadiene

e)

2,5-dimethyl-1,4-cyclohexadiene

90.

Please indicate which of the two reactants is the ELECTROPHILE for each of the two reactions?

a)

1 and 3

b)

1 and 4

c)

2 and 3

d)

2 and 4

91.

Arrange the following alkenes in order of increasing stability (least stable to most stable).

a)

3,2,1,4

b)

2,1,4,3

c)

1,2,3,4

d)

2,4,1,3

e)

1,4,2,3

92.

Consider the following energy diagram for an enzyme-catalyzed reaction.

How many intermediates are involved in the catalyzed reaction?

a)

2

b)

3

c)

4

d)

5

93.

Classify this reaction

a)

Addition

b)

Substitution

c)

Elimination

d)

Rearrangment

94.

Classify this reaction

a)

Addition

b)

Elimination

c)

Substitution

d)

Rearrangment

95.

For which of the compounds below are cis-trans isomers possible?

a)

1 only

b)

2 only

c)

1 and 2

d)

2 and 3

e)

All 3

96.

WHich of the following compounds will rotate the plane of polarized light?

a)

b)

c)

d)

e)

None of the above

97.

How many chiral centers?

a)

2

b)

3

c)

4

d)

5

e)

None of the above

98.

Which of the following is a propagation step in free radical halogenatin of alkanes?

a)

$Cl\cdot+CH_4\rightarrow\ H\cdot+CH_3Cl$

b)

$Cl\cdot+\cdot CH_3\rightarrow\ CH_3Cl$

c)

$\cdot CH_3+Cl_2\rightarrow\ Cl\cdot+CH_3Cl$

d)

$Cl_2\rightarrow\ 2\ Cl\cdot$

e)

More than one of the above.

99.

Which is the proper order for the carbocation stability (from lowest to highest stability)?

a)

1,2,3

b)

2,3,1

c)

1,3,2

d)

3,2,1

e)

None of the above

100.

Which is the correct IUPAC name for the following compound?

a)

3-ethyl-5-bromohept-3-ene

b)

5-bromo-3-ethylhept-3-ene

c)

3-bromo-5-ethylhept-4-ene

d)

1,1-diethyl-3-bromopent-1-ene

e)

None of the above

101.

Which properly defines the relationship between these molecules.

a)

Identical

b)

Enantiomers

c)

Diastereomers

d)

Constituitonal isomers

e)

Different, not isomers

102.

Which of the following would be the major product when reacting the compound in the box with HCl?

a)

b)

c)

d)

None of the above

e)

All of the above

103.

Which of the following is the most stable alkene?

a)

b)

c)

d)

104.

Which of the following cannot act as a nucleophile?

a)

b)

c)

d)

Br-

105.

What is the correct structure for (2E, 5Z)-2-bromo-5-methylocta-2,5-diene?

a)

b)

c)

d)

106.

Which of the statements about the reaction profile below is false?

a)

The reactant is more stable than the product.

b)

The first step is rate determining.

c)

The reaction is exothermic.

d)

The equilibrium constant is > 1 , greater than 1.

e)

All of the above is true.

107.

How many different monobrominated products can be made in the free radical chlorination for the following reactants?

a)

1

b)

2

c)

3

d)

4

e)

None of the above

108.

The following IR is representative of which functional group?

a)

Amine

b)

Alcohol

c)

Carboxylic Acid

d)

Amide

e)

Ketone

109.

Which of the listed reactions occur with addition that is "syn" only ( or syn sterochemistry).

a)

Halogenation

b)

Hydroboration

c)

Hydrohalogenation

d)

Acid catalyzed hydration

e)

More than of the above give syn addition only.

110.

What is the intermediate for the following reaction?

a)

Carbocation

b)

Radical

c)

Brominum bridge ion

d)

Carbene

e)

None of the above

111.

Use the following table to answer.

The given reaction is in the answer boxes, DO NOT CHOOSE THE PICTURE, choose the letter it corresponds to.

a)

b)

A

c)

B

d)

C

e)

D

112.

Use the following table to answer.

The given reaction is in the answer boxes, DO NOT CHOOSE THE PICTURE, choose the letter it corresponds to.

a)

b)

A

c)

B

d)

C

e)

D

Organic Chemistry Final Exam

Total questions: 112

Worksheet time: 28hrs 0mins

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