Free Printable Organic Chemistry Exam 3

1.

Choose the reaction that has the following;

- Markovnikov Addition

- Carbocation Intermediate

a)

Hydrohalogenation

b)

Halogenation

c)

Halohydrin Formation

d)

Oxymercuration

2.

Step 1 for the mechanism in hydrohalogenation is...

a)

b)

c)

3.

Step 2 for the mechanism in Hydrohalogenation is

a)

b)

c)

4.

Step 3 for the mechianism in Hydrohalogention is

a)

b)

c)

5.

The carbocation found in hydrohalogenation is

a)

b)

c)

6.

Step 1 in the mechanism for halogenation is

a)

b)

c)

7.

Step 2 in the mechanism for halogenation is

a)

b)

c)

8.

Step 3 in the mechanism for halogenation is

a)

b)

c)

9.

The brominuim Ion bridge found in halogenation is

a)

b)

c)

10.

Halogenation is considered...

a)

Anti Addition

b)

Syn Addition

11.

Halohydrin Formation is considered...

a)

Anti Addition

b)

Syn Addition

12.

These decribe which reaction

- Hydration from H-OH

- Acid catalyzed hydration

- Markovnikov Addition

- Rearrangement

- Harsh conditions (250°C )

a)

Halogenation

b)

Halohydrin Formation

c)

Hydrohalogenation

13.

Step 1 in the mechanism for Halohydrin Formation is

a)

b)

c)

d)

14.

Step 2 in the mechanism for Halohydrin Formation is

a)

b)

c)

d)

15.

Step 3 in the mechanism for Halohydrin Formation is

a)

b)

c)

d)

16.

Step 4 in the mechanism for Halohydrin Formation is

a)

b)

c)

d)

17.

The intermediate found in a Halohydrin Formation is a bromonium ion bridge that looks like...

a)

b)

c)

d)

18.

What is the product of this reaction?

a)

b)

c)

19.

Choose one of the following reactions:

- anti-addition of OH

-acid-catalyzed

a)

hydroxylation

b)

halogentionation

c)

bromonium bridge

d)

Simmons-smith

20.

Choose the reaction that these descriptions describe

- Mercurimium Ion Bridge

- Markovnikov still applies

- No Carbocation

- No Rearrangement

a)

Oxymercuration

b)

Halohydrin Formation

c)

Halogenation

d)

Hydrohalogenation

21.

The intermediate found in Oxymercuration is known as, the Mercurimium Ion Bridge and can look like, Choose TWO answers

a)

b)

c)

d)

22.

Which reaction is...

- Borane (BH₃) electron deficient

- Anti-Markovnikov orientation

- OH is added to carbon with most H’s

- H and OH add with syn stereochemistry

a)

Hydration by Hydroboration

b)

Hydrogenation

c)

Expoxidation

d)

Halogenation

23.

Which one of these is considered the intermediate found in Hydration by Hydroboration

a)

b)

c)

24.

Which reaction do these descriptions describe

- Addition of H-H across C=C

- Reduction is addition of H₂ or its equivalent

- Requires Pt or Pd as powders on carbon and H₂

- SYN addition

- PtO₂ , NiO₂ , PdO₂

a)

Hydrogenation

b)

Halogenation

c)

Expoxidation

d)

Hydroboration

25.

The reagent H₂ , Pt , Pd , or Ni would give us which intermediate?

a)

b)

c)

d)

26.

Which reaction do these descriptions describe

- 3 membered ring that has an oxygen in it

- 2 carbons and an oxygen

- Same side addition, Syn addition

- Cyclic Ether

- MCPBA

a)

Epoxidation

b)

Hydrogenation

c)

Hydragtion by Hydroboration

d)

Halogenation

27.

MCPBA is known as...

a)

meta-Chloroperoxy-benzoic acid

b)

1,2-Epoxy-cycloheptane

c)

Cycloheptane

28.

The structure of MCPBA looks like...

a)

b)

c)

d)

29.

what is the intermediate?

a)

b)

c)

30.

in the ozonolysis reaction, ozone (O3) is added to form what?

a)

molozonide

b)

ozonide

31.

choose one of the following reactions:

$kMnO_4,\ H_3O$

-complete oxidation

-cleavage

a)

permanganate oxidation

b)

dehydrohalogenation

c)

dehydration

32.

what is the product?

a)

b)

c)

33.

- $CHCl_3,KOH$

- it's stereospecific addition

which reaction is this?

a)

ozonolysis

b)

permanganate

c)

dichlorocarbene

d)

dehydration

34.

what reagent is used to form this product?

a)

$H^+,\ H_2O$

b)

$CHCl_3,\ KOH$

c)

$Cl_2,\ CH_3CH_2OH$

35.

what is the mechanism for Dichlorocarbene?

a)

b)

c)

36.

what is the product?

a)

b)

c)

37.

choose one of the following reactions:

-total cleavage of a double bond

a)

ozonolysis

b)

acid-catalyzed hydration

c)

simmons-smith

d)

hydroxylation

38.

what is the product?

a)

b)

c)

d)

39.

what is the intermediate?

a)

b)

c)

d)

40.

What is the product?

a)

b)

c)

d)

41.

what is the first step of Acid-catalyzed hydration mechanism?

a)

b)

c)

42.

what is the second step of the Acid-catalyzed hydration mechanism?

a)

b)

c)

43.

what is the third step of the Acid-catalyzed hydration mechanism?

a)

b)

c)

44.

- $H^+,\ H_2O$

- Carbocation intermediate

-Markovnikov

Choose from the following reactions.

a)

acid-catalyzed

b)

dichlorocarbene

c)

permanganate

d)

ozonolysis

45.

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

46.

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

47.

When $OsO_4$ reacts with a 1,2-dimethylcyclohexene double bond, we say that the reaction occurs with:

a)

Cleavage and partial oxidation

b)

Cleavage and complete oxidation

c)

Epoxidation

d)

Diol formation

e)

None of the above

48.

When $O_3$ reacts with a 3,4-dimethyl-1-hexyne double bond, we say that the reaction occurs with:

a)

Cleavage and partial oxidation

b)

Cleavage and complete oxidation

c)

Epoxidation

d)

Diol formation

e)

None of the above

49.

which of the listed reactions occur with an addition that is "syn" only?

a)

halogenation

b)

hydroboration

c)

hydrohalogenation

d)

acid-catalyzed hydration

e)

None of the above

50.

which of the listed reactions occur with an addition that is "anti" only?

a)

ozonolysis

b)

hydroboration

c)

hydrohalogenation

d)

hydrogenation

e)

none of the above

51.

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)

52.

what would be the starting material?

a)

b)

c)

d)

53.

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

a)

$H_2,\ Pd\left(C\right)$

b)

$Li,NH_3$

c)

$H_2,\ Lindlar\ catalyst\$

d)

$NaNH_2$

e)

None of the above

54.

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

(The picture shows butanone)

a)

$O_3$

b)

$KMnO_4$

c)

$BH_{3\ }then\ H_2O_2$

d)

$H_2SO_4,\ H_2O,\ HgSO_4$

e)

More than one of the above

55.

what is the intermediate for this reaction?

a)

carbocation

b)

radical

c)

bromonium bridge ion

d)

carbene

e)

none of the above.

56.

Which of the following reagents gives cis-2-butene from 2-butyne?

a)

H₂ , Pd/C

b)

Li/NH₃

c)

H₂ , Lindlar's catalyst

d)

Na⁺ ⁻NH₂

e)

None of the above

57.

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

a)

O₃

b)

KMnO₄

c)

BH₃ then H₂O₂

d)

H₂SO₄ , H₂O , HgSO₄

e)

More than one of the above

58.

Which of the listed reactions occur with addition that is "anti" ( or anti stereochemistry ) only

a)

Ozonolysis

b)

Hydroboration

c)

Hydrohalogenation

d)

Hydrogenation

e)

None of the above

59.

What is the intermediate for the following reaction

a)

Carbocation

b)

Radical

c)

Chloronium bridge ion

d)

Carbene

e)

None of the above

60.

Carbonyl Compounds are known as

a)

Ketones

b)

Amides

c)

Esters

d)

All of the above

61.

A carbon-carbon TRIPLE bond is...

a)

2200

b)

3300

c)

3400

d)

1700

62.

Alkane, carbon-hydrogen bond is...

a)

2850-2960

b)

3000

c)

3300

d)

3400

63.

Alkene, Carbon-Carbon DOUBLE bond is...

a)

3000

b)

3300

c)

3400

d)

1700

64.

Alkyne, Carbon-Carbon DOUBLE bond is...

a)

3000

b)

3300

c)

1700

d)

3400

65.

Alcohol, Oxygen-Hydrogen bond is...

a)

3400

b)

3300

c)

3000

d)

1700

66.

Carbonyl Compounds, Carbon-Oxygen Double bond is...

a)

3300

b)

3000

c)

3400

d)

1700

67.

Carbon-Oxygen single bond is...

a)

1050-1150

b)

3400-3650

c)

2850-2750

d)

2850-2960

68.

Aromatic Compound, Carbon-Carbon DOUBLE bond is...

a)

1600

b)

3300

c)

3000

d)

1700

69.

Alcohols and Amides

a)

3400-3650

b)

3000

c)

1700

d)

3300

70.

Aldehydes, 2 small peaks, 2 carbonyl-H peaks, N-H is...

a)

2850-2750

b)

3000

c)

3400

d)

1700

71.

Choose the correct product from the shown reaction

a)

b)

c)

d)

e)

None of the above

72.

Choose the correct starting material for the shown product.

a)

b)

c)

d)

e)

Organic Chemistry Exam 3

Total questions: 75

Worksheet time: 15hrs 53mins

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