CHEM-106-MIDTERM 1 (28.04.2023) 6.04.

2024 12:15

CHEM-106-MIDTERM 1 (28.04.2023)

Points: 89/100

Incorrect 0/2 Points

Enantiomers are:

non-superposable molecules that are mirror images of each other.

non-superposable constitutional isomers

molecules that have a mirror image.

non-superposable molecules.

molecules that have at least one stereogenic center.

Correct 3/3 Points

Which of the following is (2R,3S) -2-chloro-3-methylpentane?

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

II

III

Correct 3/3 Points

In which structure(s) below does the oxygen have a formal charge of +1?

I and III

I and IV

I, III and IV

II only

I only

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Correct 3/3 Points

Name the following compound:

(R,Z)-2,4-dibromo-3-methylpent-2-ene

(R,E)-2,4-dibromo-3-methylpent-2-ene

(S,E)-2,4-dibromo-3-methylpent-3-ene

(S,E)-2,4-dibromo-3-methylpent-2-ene

(R,E)-2,4-dibromo-3-methylpent-3-ene

Correct 2/2 Points

What alkyl groups make up the following ether?

ethyl and benzyl

ethyl and phenyl

None of these choices.

propyl and benzyl

propyl and phenyl

Correct 3/3 Points

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

The bond angle for the C-C-O bonds in the following molecule would be
expected to be approximately:

180°

90°

109°

145°

120°

Correct 3/3 Points

I and II are:

diastereomers.

enantiomers.

constitutional isomers.

not isomeric.

identical.

Correct 3/3 Points

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

Which molecule(s) has/have dipole moment(s) equal to zero?

Correct 3/3 Points

What prediction can be made of the relative strengths of the conjugate

bases of following acids:

Correct 2/2 Points

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

10

What is the correct IUPAC name for the following compound?

5-Ethyl-3-fluorohexanol

3-fluoro-5-methyl-7-heptanol

5-Ethyl-3-fluoro-1-hexanol

3-fluoro-5-methyl-1-heptanol

2-Ethyl-4-fluoro-6-hexanol

Correct 3/3 Points

11

What is the enantiomeric excess of a compound that shows a specific

rotation +18.6º, where the pure enantiomer has a reference value of
+24.8 º?

6.6%

50%

75%

0% rasemic mixture

21.5%

Incorrect 0/3 Points

12
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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

12

Which of these is a correct electron-dot representation of the nitrite ion?

II

III

IV

Correct 3/3 Points

13

trans-1,2-Dibromocyclohexane is represented by structure(s): I II III

II

III

II and III

I and II

Correct 3/3 Points

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

14

Give the IUPAC name for the following compound

4-Methyl-2-hexyne

3-Methyl-2-hexyne

4-Ethyl-2-pentyne

3-Methyl-4-hexyne

2-Ethyl-3-pentyne

Correct 3/3 Points

15

Which compound would have the lowest boiling point?

II

III

IV

Correct 3/3 Points

16

How many s-sp3 bonds are there in the following substance?

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

12

13

16

Correct 3/3 Points

17

Which compound is a tertiary alcohol?

II

III

IV

Correct 3/3 Points

18

The least stable conformation of 3-bromo-2-methylpentane, viewed

through the
C-2—C-3 bond (i.e., C-2 in the front, C-3 in the back):

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

II

III

IV

Correct 3/3 Points

19

Which of the following would have a trigonal planar structure?

All of these choices.

II and IV

IV and V

II, IV, and V

I, II, and IV

Correct 3/3 Points

20

The compound aspartame is a dipeptide that is often used as a sugar

substitute. Which functional groups are present in aspartame?

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

alcohol, secondary amine, ketone, ester

carboxylic acid, secondary amine, ketone, ester

ester, amide, primary amine, carboxylic acid

carboxylic acid, ester, amide, secondary amine

none of these choices

Correct 3/3 Points

21

What reactants would give the following products?

Incorrect 0/3 Points

22

Which pair of species are both bases in the following reaction?

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

Correct 3/3 Points

23

Which is the correct name for the compound shown below?

Bicyclo[2.2.0]hexane

Bicyclo[2.2.1]hexane

Bicyclo[2.2.2]hexane

Disquarane

Bicyclo[2.2.0]butane

Correct 3/3 Points

24

Identify the atomic orbitals in the C-N sigma bond in the following oxime:

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

Correct 2/2 Points

25

The compound below is an adrenocortical hormone called cortisone.

Which functional group
is NOT present in cortisone?

Carboxylic acid

1° alcohol

Ketone

Alkene

3° alcohol

Correct 3/3 Points

26

Which of the following structures represent compounds that are

constitutional isomers of each other?

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

I and II

I, II and III

I, II, III and IV

I and III

II and III

Correct 3/3 Points

27

Which of the following organic compounds has the strongest conjugate

base?

Correct 3/3 Points

28

Which one(s) is/are a meso compound?

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

II

III

I and III

I and II

Correct 3/3 Points

29

Which of the following structure is an acceptable bond libe formula for

CH3CHClCHCH2?

I and IV

I, II, and III

All of these choices

II and III

Correct 2/2 Points

30

Provide a name for the following compound

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

4-Bromo-2-chloro-2-isopropylpentane

2-Bromo-4-chloro-4-isopropylpentane

2-(2-Bromopropyl)-2-chloro-3-methylbutane

5-Bromo-3-chloro-2,3-dimethylhexane

2-Bromo-4-chloro-4,5-dimethylhexane

Correct 2/2 Points

31

n-Pentane has a higher boiling point than isopentane due to an increased

surface to surface
interaction of dispersion forces.

True

False

Correct 3/3 Points

32

Which of the structures below is not expected to contribute to the CO2

resonance hybrid?

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Incorrect 0/3 Points

33

Which of the following is the Lewis structure for CH3CO2H?

Correct 2/2 Points

34

The most stable conformation of trans-1-tert-butyl-2-methylcyclohexane

is the one in which:

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

the molecule is in the half chair conformation.

both groups are equatorial.

both groups are axial.

the methyl group is axial and the tert-butyl group is equatorial.

the tert-butyl group is axial and the methyl group is equatorial.

Correct 3/3 Points

35

Which is a 3° alkyl halide?

III

IV

II

Correct 2/2 Points

36

Which of the following is true of any (S) -enantiomer?

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CHEM-106-MIDTERM 1 (28.04.2023) 6.04.2024 12:15

It rotates plane-polarized light to the right.

It has the highest priority group on the left.

It rotates plane-polarized light to the left.

It is the mirror image of the corresponding (R) -enantiomer.

It is a racemic form.

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