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CHEM 241 - NSU - Chapter 4 - Stereochemistry

Total questions: 75

Worksheet time: 2hrs 38mins

Name
Class
Date
1.
a)

constitutional isomers

b)

enantiomers

c)

diastereomers

d)

identical

e)

none of these

2.

Identify the relationship I and II and III and IV

a)

enantiomer

b)

diastereomer

c)

identical

d)

constitutional isomer

e)

None of the structures

1
1)
3.

Identify the relationship I and V

a)

enantiomer

b)

diastereomer

c)

identical

d)

constitutional isomer

e)

different compounds

1
1)
4.
a)

I, II, III, IV, and V

b)

I, II, III, and IV

c)

I and II

d)

III and IV

e)

IV alone

5.
a)

I and II

b)

IV and V

c)

II and III

d)

I, II, and III

e)

None of the above options

6.
a)

constitutional isomers

b)

enantiomers

c)

diastereomers

d)

identical

e)

none of the above

7.
a)

II

b)

II and III

c)

II and IV

d)

III and V

e)

IV and V

8.

What is the Configuration of the Chirality Centers? (Red, Blue)

a)

(S,R)

b)

(S,S)

c)

(R,R)

d)

(R,S)

9.

What is the Relationship between these Molecules?

a)

Same Molecule

b)

Diastereomers

c)

Enantiomers

d)

Constitutional Isomers

10.

How many Stereoisomers Exist for this Molecule?

a)

One

b)

Two

c)

Three

d)

Four

11.

What is the Relationship between these Molecules?

a)

Same Molecule

b)

Diastereomers

c)

Enantiomers

d)

Constitutional Isomers

12.

Give the correct absolute configuration of this molecule

a)

(1R, 2S)-2-isopropylcyclohexanol

b)

(1R,2R)-2-isopropylcyclohexanol

c)

(1S,2R)-2-isopropylcyclohexanol

d)

(1S,2S)-2-isopropylcyclohexanol

13.

What is the relationship between the compounds?

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

14.

Choose the compound that is a constitutional isomer of this compound:

a)
b)
c)
d)
15.

What is the relationship between the compounds:

(3S,4R)-4-methylheptan-3-ol

and

(3R,5S)-5-methylheptan-3-ol

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

16.

What is the relationship between the compounds:

(3S,5R,8S)-8-chloro-5-methyldecan-3-ol

and

(3R,5S,8S)-8-chloro-5-methyldecan-3-ol

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

17.

What is the relationship between the compounds?

a)

same compound

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

18.

What is the relationship between the compounds?

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

19.

What is the relationship between the compounds?

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

20.

What is the relationship between the compounds?

a)

same compound

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

21.

What is the relationship between the compounds?

a)

same compound

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

22.

What is the relationship between the compounds?

a)

same compound

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

23.

Assume all you know about a compound is that the name is (+)-d-glucose and select all true statements. (i.e., do NOT look up information about the structure. Use the name only.)

a)

It is chiral.

b)

It has one chiral center.

c)

The enantiomer rotates plane-polarized light counterclockwise.

d)

It has three diastereomers.

e)

It rotates plane-polarized light clockwise.

24.

Select ALL meso compounds.

a)
b)
c)
d)
e)
25.

To determine the R/S configuration, the groups attached to a chiral center would go in this order for highest priority (1) to lowest (4). Listed 1-2-3-4.

a)

Br, ethyl, isopropyl, methyl

b)

methyl, ethyl, isopropyl, Br

c)

Br, ethyl, methyl, isopropyl

d)

Br, isopropyl, ethyl, methyl

26.

Select ALL compounds that are chiral.

a)
b)
c)
d)
e)
27.

You have a sample of decan-2-ol that is a mixture of the two enantiomers with 95:5 relative abundance S:R. Select the true statement.

a)

The sample will rotate plane-polarized light clockwise because S is more abundant and S always rotates the light clockwise.

b)

The sample will rotate plane-polarized light counterclockwise because S is more abundant and S always rotates the light counterclockwise.

c)

The sample will rotate plane-polarized light but you cannot know the direction without running the experiment.

d)

The sample will not rotate plane-polarized light.

28.

What is the maximum number of configurational isomers for the line structure shown?

a)

2

b)

4

c)

8

d)

16

29.

This compound has:

a)

No enantiomer and two diastereomers.

b)

One enantiomer and two diastereomers.

c)

Two enantiomers and no diastereomers.

d)

One enantiomer and one diastereomer.

30.

What is the relationship between 1,4-dichlorobutane and 1,6-dichlorohexane?

a)

unrelated

b)

enantiomers

c)

diastereomers

d)

conformational isomers

e)

constitutional isomers

31.

Determine the configuration of the following chiral centers, then name the molecule.

(a)  

32.

Determine the configuration of the following chiral centers, then name the molecule.

(a)  

33.

Determine the configuration of the following chiral centers, then name the molecule.

(a)  

34.

Compounds which have different arrangements of atoms in space while having same atoms bonded to each other are said to have

a)

position isomerism

b)

functional group isomerism

c)

chain isomerism

d)

stereoisomerism

35.

Which of the following can make difference in optical isomers?

a)

heat

b)

temperature

c)

polarized light

d)

pressure

36.

Which of the following terms best describes the following pair of molecules?

a)

Isomers

b)

Constitutional isomers

c)

Configurational isomers

d)

Geometrical isomers

37.

Which of the following molecules does not possess enantiomers?

a)

CH3CH2CH2CHBrCH3

b)

CH3CH2CBr2CH3

c)

CH3CHBrCH2CH3

d)

CHBr2CH2CHBrCH3

38.

Is it true that enantiomer have the same physical and chemical properties?

a)

Yes

b)

False

39.

Can enantiomer rotates plane-polarised light?

a)

Yes in all situations

b)

No because it is optically active

c)

Yes but it can only rotate the polarised light in opposite direction

d)

No due to its restricted rotation of carbon-carbon double bond

40.

What is the relationship between 1 and 4?

a)

diastereoisomers

b)

enantiomers

c)

no relationship

d)

meso compounds

41.

What is the relationship between 1 and 2?

a)

diastereoisomers

b)

enantiomers

c)

no relationship

d)

meso compounds

42.

Which of the following statement is FALSE about stereoisomerism?

a)

Same molecular formula

b)

Same structural formula

c)

Different structural arrangement or connectivity

d)

Different spatial arrangement

43.

An asymmetric carbon is the same as a...

a)

achiral carbon

b)

chiral carbon

c)

prochiral carbon

d)

axial carbon

44.

What property can be assigned to a carbon atom that has four different atoms or structural groups attached to it?

a)

isomerity

b)

chirality

c)

chivalry

d)

geometry

45.

Can this compound can form optical isomers?

a)

No

b)

yes

c)

depends on whether it wants to or not

46.

How many chiral centers?

a)

1

b)

3

c)

4

d)

2

47.

What is the relationship between A and B.

a)

structural isomers

b)

meso compounds

c)

diastereoisomers

d)

both have chiral carbons

48.

How many chiral centers are there?

a)

1

b)

3

c)

2

d)

6

49.

R or S configuration?

a)

R

b)

S

50.

Is it in R or S configuration?

a)

R

b)

S

51.

How many chiral centers are there?

a)

1

b)

2

c)

3

d)

4

52.

Designate whether it's an R or S configuration

a)

R

b)

S

53.

Chiral or achiral?

a)

Chiral

b)

Achiral

54.

Is it chiral or a chiral?

a)

Chiral

b)

Achiral

55.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

56.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

57.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

58.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

59.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

60.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

61.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

62.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

63.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

64.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

65.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

66.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

67.

Determine if the chiral center is R/S

a)

R

b)

S

c)

Does not have a chiral center

68.

Define the meaning chiral or stereogenic carbon.

a)

The molecule is a optically active compound.

b)

It has 4 different groups attached to it.

c)

It must have a chlorine atom attached to it.

d)

It is an alkene.

69.

Assign the configuration of the below two structures

a)

S,S

b)

S,R

c)

R,S

d)

R,R,

70.

Number of stereoisomers of camphor is

a)

2

b)

3

c)

4

d)

1

71.

The given compounds 1 and 2 are

a)

Identical

b)

Diastereomers

c)

Enantiomers

d)

Constitutional isomers

72.

Which one of the following is optically active

a)

d

b)

a

c)

b

d)

c

73.

The correct statement about optical activity is

a)

a molecule having two or more chiral centers is always optically active

b)

a molecule having just one chiral center is always optically active

c)

a molecule having alternating axis of symmetry is optically inactive is always optically active

d)

an optically active molecule should have atleast one chiral center

74.

The maximum number of stereoisomers possible for 4-phenyl but-3-en-2ol is

a)

1

b)

2

c)

3

d)

4

75.

A racemic mixture is optically active.

a)

yes

b)

no

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