Essential Organic Chemistry 2nd Edition Bruice-Test Bank

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Essential Organic Chemistry 2nd Edition Bruice-Test Bank

Essential Organic Chemistry, 2e (Bruice)


Chapter 2


Acids and Bases


1)
 

Which of the following is not a conjugate acid-base pair?

 

  1. A)

 

 

 

  1. B)

 

 

 

  1. C)

 

HSO-4, H2SO4

 

  1. D)

 

-OH, O2-

 

  1. E)

 

NO3-, NO2-

 

Answer:
 

E

 

Section:


2.1


2)
 

Which is defined as a species that accepts a proton?

 

  1. A)

 

Arrenhius acid

 

  1. B)

 

Lewis acid

 

  1. C)

 

Lewis base

 

  1. D)

 

Bronsted-Lowry acid

 

  1. E)

 

Bronsted-Lowry base

 

Answer:
 

E

 

Section:


2.1


3)
 

What is the product formed from the following acid-base reaction?

 

 

 

  1. A)

 

CH3O-   +   +NH4

 

  1. B)

 

CH2OH   +   +NH3

 

  1. C)

 

CH3OH2+   +   -NH2

 

  1. D)

 

CH3NH2   +   H2O

 

  1. E)

 

CH4   +   NH2OH

 

Answer:
 

A

 

Section:


2.1


4)
 

The conjugate acid of H2O is __________.

 

  1. A)

 

 

 

  1. B)

 

H3O

 

  1. C)

 

 

 

  1. D)

 

 

 

  1. E)

 

 

 

Answer:
 

C

 

Section:


2.1


5)
 

Which of the following ions is the strongest acid?

 

  1. A)

 

 

 

 

  1. B)

 

 

 

 

  1. C)

 

 

 

 

  1. D)

 

H2O

 

  1. E)

 

 

 

Answer:
 

E

 

Section:


2.1


6)
 

The conjugate base of NH3 is __________.

 

  1. A)

 

+NH2

 

  1. B)

 

-NH2

 

  1. C)

 

+NH4

 

  1. D)

 

-NH4

 

  1. E)

 

-NH3

 

Answer:
 

B

 

Section:


2.1


7)
 

Which species act as bases in the following reaction?

 

 

 

  1. A)

 

1 and 2

 

  1. B)

 

3 and 4

 

  1. C)

 

2 and 4

 

  1. D)

 

1 and 3

 

  1. E)

 

2 and 3

 

Answer:
 

C

 

Section:


2.1


8)
 

What is the conjugate acid of NH3?

 

  1. A)

 

+NH3

 

  1. B)

 

-NH

 

  1. C)

 

+NH4

 

  1. D)

 

-NH2

 

  1. E)

 

+NH2

 

Answer:
 

C

 

Section:


2.1


9)
 

Give the conjugate acid and the conjugate base for HSO4-.

 

Answer:
 

conjugate acid:  H2SO4

conjugate base:  SO4-2

 

Section:


2.1


10)
 

Write a completed equation for the acid-base pair shown below.

 

HCO2H + -NH2 →

 

Answer:
 

HCO2H + -NH2 → HCO2- + NH3

 

Section:


2.1


11)
 

What is the conjugate acid of CH3NH2?

 

  1. A)

 

CH3NH3+

 

  1. B)

 

CH3NH-

 

  1. C)

 

NH4+

 

  1. D)

 

NH2-

 

Answer:
 

A

 

Section:


2.1


12)
 

What is the conjugate base of CH3NH2?

 

  1. A)

 

CH3NH3+

 

  1. B)

 

CH3NH-

 

  1. C)

 

NH4+

 

  1. D)

 

NH2-

 

Answer:
 

B

 

Section:


2.1


13)
 

What is the pH of a 0.1 M solution of HCl? (Note: pKa for HCl is -6.)

 

  1. A)

 

6

 

  1. B)

 

-6

 

  1. C)

 

1

 

  1. D)

 

-8

 

  1. E)

 

-1

 

Answer:
 

C

 

Section:


2.2


14)
 

If the pH of a solution of HCl is 4.1, then what is the H3O+ concentration?

 

  1. A)

 

-0.6128

 

  1. B)

 

6.1 × 10-1

 

  1. C)

 

7.9 × 10-5

 

  1. D)

 

1.3 × 10-10

 

  1. E)

 

8.0 × 109

 

Answer:
 

C

 

Section:


2.2


15)
 

Which statement is correct about acid-base chemistry?

 

  1. A)

 

the larger the Ka, the stronger the acid

 

  1. B)

 

a small pKa correspond to a large Ka

 

  1. C)

 

the smaller the pKa, the stronger the acid

 

  1. D)

 

A only

 

  1. E)

 

all of the above

 

Answer:
 

E

 

Section:


2.2


16)
 

If H2O has a pKa value of 15.7 and HF has a pKa value of 3.2, which is a stronger base, HO- or F-? Explain.

 

Answer:
 

HO- is a stronger base than F- because HF is a stronger acid than H2O, and the stronger the acid, the weaker its conjugate base.

 

Section:


2.2


17)
 

How is the position of equilibrium determined in an acid-base reaction?

 

Answer:
 

Compare the p value of the acid on the left side of the reaction arrow to the pKa value of the acid on the right side of the reaction arrow. The equilibrium favors reaction of the strong acid and formation of the weak acid.  “Strong reacts to give weak”.

 

Section:


2.2


18)
 

The pKa of CH3COOH is 4.8 and the pKa of HCOOH is 3.8.  Given this information, one knows that __________.

 

  1. A)

 

CH3COOH completely ionizes in water

 

  1. B)

 

HCOOH is a weaker acid than CH3COOH

 

  1. C)

 

HCOO- is a weaker base than CH3COO-

 

  1. D)

 

CH3COOH reacts with HO- while HCOOH does not

 

  1. E)

 

HCOOH reacts with HO- while CH3COOH does not

 

Answer:
 

C

 

Section:


2.2


19)
 

What is the typical pH of rain?

 

  1. A)

 

1.0

 

  1. B)

 

4.0

 

  1. C)

 

5.5

 

  1. D)

 

7.0

 

  1. E)

 

7.5

 

Answer:
 

C

 

Section:


2.2


20)
 

Which of the following is the strongest acid?

 

  1. A)

 

CH3OH

 

  1. B)

 

CH3OH2+

 

  1. C)

 

H2N-

 

  1. D)

 

CH3NH2

 

  1. E)

 

CH3NH3+

 

Answer:
 

B

 

Section:


2.3


21)
 

Which of the following is the strongest acid?

 

 

  1. A)

 

I

 

  1. B)

 

II

 

  1. C)

 

III

 

  1. D)

 

IV

 

  1. E)

 

V

 

Answer:
 

E

 

Section:


2.3 and 2.6


22)
 

Which of the following statements is correct?

 

  1. A)

 

The stronger the acid, the weaker its conjugate base.

 

  1. B)

 

The stronger the acid, the stronger its conjugate base.

 

  1. C)

 

The stronger the base, the stronger its conjugate base.

 

  1. D)

 

The stronger the acid, the weaker its conjugate acid.

 

  1. E)

 

The stronger the acid, the stronger its conjugate acid.

 

Answer:
 

A

 

Section:


2.3


23)
 

Which of the following is the strongest acid?

 

  1. A)

 

HI

 

  1. B)

 

H2O

 

  1. C)

 

:NH3

 

  1. D)

 

CH4

 

  1. E)

 

CH3OH

 

Answer:
 

A

 

Section:


2.3


24)
 

Which of the following is the strongest acid?

 

  1. A)

 

CH3CH2OH

 

  1. B)

 

CH3OCH3

 

  1. C)

 

CH3NHCH3

 

  1. D)

 

CH3CCH

 

  1. E)

 

CH3CHCH2

 

Answer:
 

A

 

Section:


2.3


25)
 

Which statement is incorrect?

 

  1. A)

 

A protonated compound has gained a proton.

 

  1. B)

 

A protonated compound has gained an electron.

 

  1. C)

 

A protonated acids are very strong acids.

 

  1. D)

 

An amine can behave as an acid or a base.

 

  1. E)

 

Alcohols are much weaker acids than carboxylic acids.

 

Answer:
 

B

 

Section:


2.3


26)
 

The pKa of CH3COOH is 4.8.  If the pH of an aqueous solution of CH3COOH and CH3COO- is 4.8, then one knows __________.

 

  1. A)

 

CH3COOH is completely ionized

 

  1. B)

 

[CH3COOH] > [CH3COO-]

 

  1. C)

 

[CH3COOH] = [CH3COO-]

 

  1. D)

 

[CH3COOH] < [CH3COO-]

 

  1. E)

 

CH3COOH is completely unionized

 

Answer:
 

C

 

Section:


2.4


27)
 

Explain why CH3CH2OH (pKa = 15.9) predominates in a solution of pH 4.5.

 

Answer:
 

The pH of the solution is more acidic than the pKa of the OH group (15.9). A compound will mainly exist in its acidic form (with its proton) in solutions that are more acidic than the pKa value of the group that undergoes dissociation (pH is less than pKa).

 

Section:


2.4


28)
 

When a small amount of hexanoic acid [CH3(CH2)4CO2H, pKa~4.8], is added to a separatory funnel which contains the organic solvent diethyl ether and water with a pH of 2.0, it is found mainly in the __________ phase as __________.

 

  1. A)

 

ether; CH3(CH2)4CO2-

 

  1. B)

 

water; CH3(CH2)4CO2-

 

  1. C)

 

ether; CH3(CH2)4CO2H

 

  1. D)

 

water; CH3(CH2)4CO2H

 

  1. E)

 

none of the above

 

Answer:
 

C

 

Section:


2.4


29)
 

When a small amount of hexanoic acid [CH3(CH2)4CO2H, pKa~4.8], is added to a separatory funnel which contains the organic solvent diethyl ether and water with a pH of 12.0, it is found mainly in the __________ phase as __________.

 

  1. A)

 

ether; CH3(CH2)4CO2-

 

  1. B)

 

water; CH3(CH2)4CO2-

 

  1. C)

 

ether; CH3(CH2)4CO2H

 

  1. D)

 

water; CH3(CH2)4CO2H

 

  1. E)

 

none of the above

 

Answer:
 

B

 

Section:


2.4


30)
 

To determine the position of equilibrium for an acid-base reaction, the equilibrium favors __________.

 

  1. A)

 

reaction of the weaker acid and formation of the stronger acid

 

  1. B)

 

shift of the reaction toward the compound with the lowest Ka

 

  1. C)

 

shift of the reaction toward the side of the reaction with the largest pKa

 

  1. D)

 

reaction of the stronger acid and formation of the weaker acid

 

  1. E)

 

None of the statements are true.

 

Answer:
 

D

 

Section:


2.5


31)
 

Explain why :NF3 is a weaker base than :NH3.

 

Answer:
 

Fluorine has an electron withdrawing effect that reduces the availability of the pair of electrons on nitrogen. Thus the basicity of :NF3 is less than that of :NH3.

 

Section:


2.6


32)
 

Consider the set of compounds, NH3, HF, and H2O. Rank these compounds in order of increasing acidity and discuss your rationale.

 

Answer:
 

NH3 < H2O < HF

 

When determining relative acidity, it is often useful to look at the relative basicity of the conjugate bases. The stronger the acid, the weaker (more stable, less reactive) the conjugate base. In this case, one would look at the relative basicity of F-, OH-, and NH2-. The relative strengths of these species can be gauged based on the electronegativity of the charged atom in each base. Since fluorine is the most electronegative, F- is the most stable, least reactive base in the group. This means that its conjugate acid, HF, is the strongest.

 

Section:


2.6


33)
 

Would you predict trifluoromethanesulfonic acid, CF3SO3H, to be a stronger or weaker acid than methanesulfonic acid, CH3SO3H? Explain your reasoning.

 

Answer:
 

Trifluoromethanesulfonic acid is a stronger acid. Compare the strengths of the conjugate bases and remember that the weaker the base, the stronger the conjugate acid. In the case of the trifluoro derivative, the presence of the highly electronegative fluorine atoms serves to delocalize the negative charge to a greater extent. This additional delocalization makes trifluoromethanesulfonate anion a weaker base. Also the electron withdrawing effect of the CF3 allows the proton to be more easily pulled off of the CF3SO3H molecule.

 

Section:


2.6


34)
 

The stronger the acid __________.

 

  1. A)

 

the less stable its conjugate base

 

  1. B)

 

the larger the pKa

 

  1. C)

 

the weaker its conjugate base

 

  1. D)

 

the larger the pH

 

  1. E)

 

the higher the concentration of hydroxide ions

 

Answer:
 

C

 

Section:


2.6


35)
 

The stability of a base is determined by which of the following?

 

  1. A)

 

pH

 

  1. B)

 

size

 

  1. C)

 

electronegativity

 

  1. D)

 

B and C

 

  1. E)

 

C only

 

Answer:
 

D

 

Section:


2.6


36)
 

What form will predominate in a solution of pH = 5.5?

 

  1. A)

 

HCN (pKa = 9.1)

 

  1. B)

 

CH3COOH (pKa = 4.76)

 

  1. C)

 

CH3CH2NH3+ (pKa = 11.0)

 

  1. D)

 

+NH4 (pKa = 9.4)

 

Answer:
 

B

 

Section:


2.7


37)
 

Which of the following is the definition of a buffer solution?

 

  1. A)

 

solution composed of a weak acid and a weak base

 

  1. B)

 

solution composed of a weak acid and its conjugate base

 

  1. C)

 

solution that can maintain a nearly constant pH even with addition of small amounts of acid or base

 

  1. D)

 

solution containing -OH ions at a pH greater than 7

 

  1. E)

 

B and C

 

Answer:
 

E

 

Section:


2.8


38)
 

Which blood buffer controls the pH of blood?

 

  1. A)

 

HSO3-/SO32-

 

  1. B)

 

H3O+/H2O

 

  1. C)

 

H2CO3/HCO3-

 

  1. D)

 

NH4+/NH3

 

  1. E)

 

HSO4-/SO42-

 

Answer:
 

C

 

Section:


2.8


39)
 

Which of the following are Lewis bases?

 

  1. A)

 

NF3

 

  1. B)

 

BF3

 

  1. C)

 

CH3OCH3

 

  1. D)

 

A and B

 

  1. E)

 

A and C

 

Answer:
 

E

 

Section:


2.9


40)
 

Explain why AlCl3 is a Lewis acid.

 

Answer:
 

A Lewis acid is an electron pair acceptor. Aluminum in AlCl3 has an empty p orbital that can accommodate the pair of electrons provided by a Lewis base.

 

Section:


2.9


Essential Organic Chemistry, 2e (Bruice)


Chapter 10


Reactions of Alcohols, Amines, Ethers, and Epoxides


1)
 

What is the functional group in an alcohol?

 

  1. A)

 

carbon-carbon double bond

 

  1. B)

 

NH2

 

  1. C)

 

OH

 

  1. D)

 

halogen

 

  1. E)

 

COOH

 

Answer:
 

C

 

Section:


10.1


2)
 

Which of the following compounds does not have the molecular formula C6H14O?

 

  1. A)

 

1-hexanol

 

  1. B)

 

2-hexanol

 

  1. C)

 

3-methyl-2-pentanol

 

  1. D)

 

3-methyl-3-pentanol

 

  1. E)

 

cyclohexanol

 

Answer:
 

E

 

Section:


10.1


3)
 

What is the IUPAC name for the following structure?

 

 

 

  1. A)

 

4-sec-hexyl-5-methyl-3-hexanol

 

  1. B)

 

3-hydroxy-4-isobutyl-5-ethyloctane

 

  1. C)

 

5-ethyl-4-isopropyl-3-octanol

 

  1. D)

 

3-hydorxy-4-isobutyl-5-propylheptane

 

  1. E)

 

3-propyl-4-isopropyl-5-heptanol

 

Answer:
 

C

 

Section:


10.1


4)
 

Give the IUPAC name for the structure below:

 

 

Answer:
 

cis-3-sec-butylcyclopentanol

 

Section:


10.1


5)
 

What is the IUPAC name of the structure below?

 

 

 

 

  1. A)

 

5-chloro-5-ethyl-3-hexanol

 

  1. B)

 

2-chloro-2-ethyl-4-hydroxyhexane

 

  1. C)

 

5-chloro-5-ethyl-3-hydroxyhexane

 

  1. D)

 

5-chloro-5-methyl-3-heptanol

 

  1. E)

 

3-chloro-3-methyl-5-heptanol

 

Answer:
 

D

 

Section:


10.1


6)
 

Give the IUPAC name for the following structure:

 

 

 

 

  1. A)

 

3-chloro-2-methylcyclohexanol

 

  1. B)

 

2-methyl-5-chlorocyclhexanol

 

  1. C)

 

1-chloro-4-methylcyclohexanol

 

  1. D)

 

5-chloro-2-methylcyclohexanol

 

  1. E)

 

2-methyl-3-chlorocyclohexanol

 

Answer:
 

D

 

Section:


10.1


7)
 

What is the IUPAC name for the following structure?

 

CH3CH(CH3)CH2CH(OH)CH3

 

 

  1. A)

 

4-methyl-2-pentanol

 

  1. B)

 

2-methyl-2-hexanol

 

  1. C)

 

2-methyl-4-pentanol

 

  1. D)

 

2-methyl-3-pentanol

 

Answer:
 

A

 

Section:


10.1


8)
 

Which of the following is a secondary alcohol?

 

  1. A)

 

3-ethyl-2-methyl-1-pentanol

 

  1. B)

 

3-ethyl-2-methyl-2-heptanol

 

  1. C)

 

3-methyl-2-hexanol

 

  1. D)

 

1-hexanol

 

Answer:
 

C

 

Section:


10.2


9)
 

Which of the following is the best method for preparing CH3Br?

 

  1. A)

 

CH3OH + Br-

 

  1. B)

 

CH3OH + HBr

 

  1. C)

 

CH3OH + Br2

 

  1. D)

 

CH3OH + NaBr

 

  1. E)

 

CH3OH + Br+

 

Answer:
 

B

 

Section:


10.2


10)
 

Why are alcohols typically poor electrophiles?

 

Answer:
 

The hydroxide ion, a relatively strong base, is a very poor leaving group.

 

Section:


10.2


11)
 

Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation.

 

CH3(CH2)6CH2OH + HBr →

 

Answer:
 

 

 

 

Section:


10.2


12)
 

Provide the structure of the major organic product in the reaction below.

 

 

 

Answer:
 

 

 

 

Section:


10.2


13)
 

Name and provide the structure of the major organic product which results when (R)-3,3-dimethyl-2-butanol is heated in the presence of HBr.

 

Answer:
 

2-bromo-2,3-dimethylbutane

 

 

 

Section:


10.1 and 10.2


14)
 

Which of the following alcohols dehydrates with the fastest rate?

 

 

 

  1. A)

 

I

 

  1. B)

 

II

 

  1. C)

 

III

 

  1. D)

 

IV

 

  1. E)

 

V

 

Answer:
 

B

 

Section:


10.3


15)
 

What is the major product of the following reaction?

 

 

 

 

 

  1. A)

 

I

 

  1. B)

 

II

 

  1. C)

 

III

 

  1. D)

 

IV

 

  1. E)

 

V

 

Answer:
 

B

 

Section:


10.3


16)
 

Which of the following alcohols, when heated with H2SO4, will undergo dehydration more rapidly? Explain.

 

 

 

Answer:
 

  1. b) will undergo dehydration more rapidly because it produces a secondary benzylic carbocation, which is more stable than secondary carbocation.

 

Section:


10.3


17)
 

What is the major product for the following reaction?

 

 

 

Answer:
 

 

 

 

 

Section:


10.3


18)
 

Rank the following alcohols in decreasing order of relative ease of dehydration:

 

 

 

  1. A)

 

A > B > C > D

 

  1. B)

 

D > C > A > B

 

  1. C)

 

C > A > D > B

 

  1. D)

 

B > D > C > A

 

  1. E)

 

A > C > D > B

 

Answer:
 

D

 

Section:


10.3


19)
 

Draw all likely products of the following reaction, and circle the product you expect to predominate.

 

2-pentanol

 

Answer:
 

 

 

 

Section:


10.3


20)
 

What is the major product of the following reaction?

 

 

 

Answer:
 

 

 

Section:


10.3


21)
 

Provide the structure of the major organic product of the following reaction.

 

 

 

Answer:
 

 

 

 

Section:


10.3


22)
 

Which of the following alcohols is oxidized to a ketone by chromic acid?

 

 

 

  1. A)

 

I

 

  1. B)

 

II

 

  1. C)

 

III

 

  1. D)

 

IV

 

  1. E)

 

V

 

Answer:
 

B

 

Section:


10.4


23)
 

Which of the following reagents can be used to oxidize 1° alcohols to aldehydes?

 

  1. A)

 

KMnO4

 

  1. B)

 

MnO2

 

  1. C)

 

K2Cr2O7

 

  1. D)

 

H2O2

 

  1. E)

 

PCC

 

Answer:
 

E

 

Section:


10.4


24)
 

What is PCC and what is it used for?

 

Answer:
 

PCC is pyridinium chlorochromate, a mixture of chromic anhydride (CrO3) and an equivalent of HCl dissolved in pyridine. It is a mild oxidizing agent used to convert alcohols to aldehydes.

 

Section:


10.4


25)
 

Describe the difference between oxidation of a primary alcohol using PCC in CH2Cl2 versus oxidation of the same primary alcohol using Na2Cr2O7 in H2SO4.

 

Answer:
 

A primary alcohol in the presence of PCC and CH2Cl2 will result in an aldehyde product whereas the same primary alcohol in the presence of Na2Cr2O7 and H2SO4 will result in a carboxylic acid after further oxidation.

 

Section:


10.4


26)
 

Provide the structure of the major organic product in the reaction below.

 

 

 

Answer:
 

 

 

 

Section:


10.4


27)
 

Provide the structure of the major organic product in the reaction below.

 

 

 

Answer:
 

 

 

 

Section:


10.4


28)
 

Provide the structure of the major organic product in the reaction below.

 

 

 

Answer:
 

No reaction. Tertiary alcohols are not oxidized by PCC.

 

Section:


10.4


29)
 

Provide the structure of the major organic product in the reaction below.

 

(CH3)3CCH2CH2OH

 

 

Answer:
 

(CH3)3CCH2CO2H

 

Section:


10.4


30)
 

Provide the structure of the major organic product in the reaction below.

 

 

 

Answer:
 

 

 

 

Section:


10.4


31)
 

Provide the major organic product of the following.

 

 

 

Answer:
 

 

 

 

Section:


10.4


32)
 

In the chromic acid oxidation of alcohols, the chromium is __________.

 

  1. A)

 

reduced from Cr+6 to Cr+3

 

  1. B)

 

oxidized from Cr+6 to Cr+3

 

  1. C)

 

reduced from Cr+3 to Cr+6

 

  1. D)

 

oxidized from Cr+3 to Cr+6

 

  1. E)

 

none of the above

 

Answer:
 

A

 

Section:


10.4


33)
 

What series of synthetic steps could be used to prepare 3-hexanol from 1-propanol?

 

Answer:
 

1)    PCC

2)    CH3CH2CH2MgBr

3)    H3O+

or

1)    HBr or PBr3

2)    Mg, Et2O

3)    CH3CH2CHO

 

Section:


10.4


34)
 

What series of synthetic steps could be used to prepare PhCHOHCH2CH3 from PhCH2OH?

 

Answer:
 

1)    PCC

2)    CH3CH2MgBr

3)    H3O+

 

Section:


10.4


35)
 

What series of synthetic steps could be used to carry out the transformation shown below?

 

 

 

Answer:
 

1)    BH3

2)    H2O2, -OH

3)    PCC

 

Section:


10.4


36)
 

When the optically active alcohol below is oxidized by H2CrO4, the major product is __________.

 

 

 

  1. A)

 

a ketone which is meso and optically inactive

 

  1. B)

 

an optically active ketone

 

  1. C)

 

a racemic mixture of ketones which is optically inactive

 

  1. D)

 

an aldehyde which is meso and optically active

 

  1. E)

 

an acyclic carboxylic acid

 

Answer:
 

B

 

Section:


10.4


37)
 

Provide the major organic product of the following.

 

 

 

Answer:
 

 

 

 

Section:


10.4


38)
 

Rank the following compounds in decreasing order of relative reactivity under acidic conditions:

 

 

 

  1. A)

 

C > A > D > B

 

  1. B)

 

D > B > C > A

 

  1. C)

 

B > D > A > C

 

  1. D)

 

A > C > B > D

 

  1. E)

 

A > B > D > C

 

Answer:
 

C

 

Section:


10.5


39)
 

Which of the following is a quaternary ammonium ion?

 

  1. A)

 

 

 

 

  1. B)

 

 

 

 

  1. C)

 

 

 

 

  1. D)

 

 

 

 

  1. E)

 

 

 

 

Answer:
 

E

 

Section:


10.5


40)
 

Alcohols are less reactive than amines.

 

Answer:
 

FALSE

 

Section:


10.5


41)
 

Which of the following is the leaving group of an amine?

 

  1. A)

 

OH

 

  1. B)

 

NH2-

 

  1. C)

 

COOH

 

  1. D)

 

NH3

 

  1. E)

 

NH4+

 

Answer:
 

B

 

Section:


10.5


42)
 

Which of the following is diisopropyl ether?

 

 

  1. A)

 

CH3CH2CH2-O-CH2CH2CH3

 

  1. B)

 

 

 

  1. C)

 

 

 

  1. D)

 

 

 

  1. E)

 

none of the above

 

Answer:
 

D

 

Section:


10.6


43)
 

Which of the following is the correct structure for 2-isopropoxy-4-ethylheptane?

 

 

  1. A)

 

 

 

 

  1. B)

 

 

 

 

  1. C)

 

 

 

 

  1. D)

 

 

 

 

  1. E)

 

 

 

 

Answer:
 

D

 

Section:


10.6


44)
 

Draw all ethers with a molecular formula of C4H10O.

 

Answer:
 

 

 

Section:


10.6


45)
 

What are the major products from the following reaction?

 

 

 

 

  1. A)

 

I

 

  1. B)

 

II

 

  1. C)

 

III

 

  1. D)

 

IV

 

  1. E)

 

V

 

Answer:
 

B

 

Section:


10.7


46)
 

When dipentyl ether is treated with excess HI, through what type of mechanism(s) does the major product result?

 

  1. A)

 

SN2

 

  1. B)

 

SN1

 

  1. C)

 

both SN1 and SN2

 

  1. D)

 

E1

 

  1. E)

 

E2

 

Answer:
 

A

 

Section:


10.7


47)
 

Provide the structure of the major organic product of the following reaction.

 

 

 

Answer:
 

 

 

 

Section:


10.7


48)
 

Propose a mechanism for the following reaction:

 

 

 

Answer:
 

 

 

 

Section:


10.8


49)
 

Provide the structure of the major organic product of the following reaction.

 

 

 

Answer:
 

 

 

 

Section:


10.8


50)
 

What is/are the product(s) from the following reaction?

 

 

 

 

  1. A)

 

I

 

  1. B)

 

II

 

  1. C)

 

III

 

  1. D)

 

IV

 

  1. E)

 

V

 

Answer:
 

A

 

Section:


10.8


51)
 

What is the major product from the following reaction?

 

 

 

 

  1. A)

 

I

 

  1. B)

 

II

 

  1. C)

 

III

 

  1. D)

 

IV

 

  1. E)

 

V

 

Answer:
 

B

 

Section:


10.8


52)
 

What is the major product for the following reaction?

 

 

 

 

  1. A)

 

I

 

  1. B)

 

II

 

  1. C)

 

III

 

  1. D)

 

IV

 

  1. E)

 

V

 

Answer:
 

D

 

Section:


10.8


53)
 

What is the major product for the following reaction?

 

 

 

 

  1. A)

 

I

 

  1. B)

 

II

 

  1. C)

 

III

 

  1. D)

 

IV

 

  1. E)

 

V

 

Answer:
 

E

 

Section:


10.8


54)
 

Provide the major organic product in the reaction below.

 

 

 

Answer:
 

 

 

 

Section:


10.8


55)
 

Provide the major organic product in the reaction below.

 

 

 

Answer:
 

 

 

 

Section:


10.8


56)
 

Provide the structure of the major organic product of the following reaction.

 

 

 

Answer:
 

 

 

 

Section:


10.8


57)
 

How are certain arene oxides believed to cause cancer?

 

Answer:
 

2′-Deoxyguanosine, a component of DNA, is a nucleophile and reacts with certain arene oxides to form a covalent bond. Once this part of DNA has formed a covalent bond to another compound, the structure and replication of the DNA is disrupted. The genetic code can no longer be transcribed properly, and this can lead to cancerous mutations.

 

Section:


10.9


Essential Organic Chemistry, 2e (Bruice)


Chapter 20


The Chemistry of the Nucleic Acids


1)
 

Where was DNA first isolated?

 

Answer:
 

from the nuclei of white blood cells.

 

Section:


20.0


2)
 

Define a “nucleoside.”

 

Answer:
 

A compound containing a base bonded to D-ribose or to 2-deoxy-D-ribose.

 

Section:


20.1


3)
 

Define a “nucleotide.”

 

Answer:
 

It is a nucleoside with either the 5′- or 3′-OH group bonded in an ester linkage to phosphoric acid.

 

Section:


20.1


4)
 

Which of the following are known as pyrimidines?

 

  1. A)

 

cytosine and thymine

 

  1. B)

 

adenine and cytosine

 

  1. C)

 

adenine and thymine

 

  1. D)

 

guanine and thymine

 

  1. E)

 

adenine and guanine

 

Answer:
 

A

 

Section:


20.1


5)
 

Which of the following bases distinguish DNA from RNA?

 

  1. A)

 

adenine and cytosine

 

  1. B)

 

guanine and uracil

 

  1. C)

 

thymine and uracil

 

  1. D)

 

uracil and guanine

 

  1. E)

 

adenine and thymine

 

Answer:
 

C

 

Section:


20.1


6)
 

Which of the following is the proper name of the nucleoside made from adenine and found in DNA?

 

  1. A)

 

adenosine

 

  1. B)

 

2′-deoxyadenosine

 

  1. C)

 

2-deoxyadenosine

 

  1. D)

 

2′-oxyadenosine

 

  1. E)

 

2′-deoxyadenine

 

Answer:
 

B

 

Section:


20.1


7)
 

When phosphoric acid is heated, it loses water to form an anhydride known as pyrophosphate or pyrophosphoric acid. What is the structure of pyrophosphoric acid?

 

  1. A)

 

 

 

 

  1. B)

 

 

 

 

  1. C)

 

 

 

 

  1. D)

 

 

 

 

  1. E)

 

 

 

 

Answer:
 

B

 

Section:


20.1


8)
 

What is a nucleoside? Give an example.

 

Answer:
 

A nucleoside is a base plus a sugar.

 

 

 

Section:


20.1


9)
 

What is a nucleotide? Give an example.

 

Answer:
 

A nucleotide is a nucleoside with one of its OH groups bonded to phosphoric acid in an ester linkage. Nucleotides of RNA are called ribonucleotides while the nucleotides of DNA are called deoxyribonucleotides.

 

 

 

Section:


20.1


10)
 

What are the four common ribonucleosides?

 

Answer:
 

cytidine, uridine, adenosine, and guanosine

 

Section:


20.1


11)
 

What is the major structural difference between a ribonucleoside and a ribonucleotide?

 

Answer:
 

A ribonucleotide is a ribonucleoside which has been phosphorylated at the oxygen attached to its 5′ carbon

 

Section:


20.1


12)
 

Besides a possible difference in base structure, what is the major structural difference between ribo- and deoxyribonucleosides?

 

Answer:
 

Deoxyribonucleosides have a hydrogen instead of a hydroxyl group at the C2 position of the sugar.

 

Section:


20.1


13)
 

Name the two pyrimidine bases which serve as components in deoxyribonucleotides.

 

Answer:
 

cytosine and thymine

 

Section:


20.1


14)
 

Name the two purine bases which serve as components in ribonucleosides.

 

Answer:
 

adenine and guanine

 

Section:


20.1


15)
 

Show that you understand how the structural components of DNA are bonded together by drawing a linear segment that contains 3 base residues.

 

Answer:
 

Other choices for the base components are possible.

 

 

 

Section:


20.1


16)
 

Which of the following statements concerning DNA, RNA, and their components is (are) not correct?

 

  1. A)

 

Phosphoric acid has three dissociable OH groups which can also react with alcohols to form phosphoesters.

 

  1. B)

 

Across the DNA helix, purine bases hydrogen bond only to other purine bases.

 

  1. C)

 

The two substituted pyrimidines in DNA are cytosine and thymine.

 

  1. D)

 

both B and C

 

  1. E)

 

none of the above

 

Answer:
 

B

 

Section:


20.1


17)
 

Identify the nucleoside shown below.

 

 

 

  1. A)

 

adenosine

 

  1. B)

 

guanosine

 

  1. C)

 

cytidine

 

  1. D)

 

uridine

 

  1. E)

 

thymidine

 

Answer:
 

B

 

Section:


20.1


18)
 

Draw the structure of 2′-deoxycytidine 3′-monophosphate.

 

Answer:
 

 

 

 

Section:


20.1


19)
 

Draw the structure of UDP.

 

Answer:
 

 

 

 

Section:


20.1


20)
 

Define a “nucleic acid.”

 

Answer:
 

Chains of five-membered-ring sugars linked by forming a phosphodiester with phosphoric acid.

 

Section:


20.1 and 20.2


21)
 

Describe the primary structure of DNA.

 

Answer:
 

DNA consists of two strands of nucleic acids with the sugar-phosphate backbone on the outside and the bases on the inside. H-bonds hold the chains together between the bases on the two strands. Adenine and thymine are always paired and guanine and cytosine are always paired.

 

Section:


20.2


22)
 

Which of the following statements explains what nucleic acids are?

 

  1. A)

 

They are acidic in nature.

 

  1. B)

 

They are the carriers of genetic information.

 

  1. C)

 

DNA and RNA are collectively known as nucleic acids.

 

  1. D)

 

Nucleic acids are chains of five-membered ring sugars, each bonded to a heterocyclic amine, linked by phosphate groups.

 

  1. E)

 

all of the above

 

Answer:
 

E

 

Section:


20.2


23)
 

Which of the following phosphate groups is found in nucleic acids?

 

  1. A)

 

 

 

 

  1. B)

 

 

 

 

  1. C)

 

 

 

 

  1. D)

 

 

 

 

  1. E)

 

 

 

 

Answer:
 

C

 

Section:


20.2


24)
 

Which of the following reaction sequences best describes the formation of the nucleic acid in the biosynthesis of DNA?

 

  1. A)

 

nucleophilic attack of a 5′-OH group of one nucleotide on the β-phosphorus of another

 

  1. B)

 

nucleophilic attack of a 5′-OH group of one nucleotide on the α-phosphorus of another

 

  1. C)

 

nucleophilic attack of a 3′-OH group of a nucleotide on the γ-phosphorus of another

 

  1. D)

 

nucleophilic attack of a 3′-OH group of one nucleotide on the β-phosphorus of another

 

  1. E)

 

nucleophilic attack of a 3′-OH group of one nucleotide on the α-phosphorus of another

 

Answer:
 

E

 

Section:


20.2


25)
 

Which of the following constitutes the primary structure of a nucleic acid?

 

  1. A)

 

the sequence of the bases in the strand

 

  1. B)

 

the sequence of the riboses in the strand

 

  1. C)

 

the sequence of the deoxyriboses in the strand

 

  1. D)

 

the sequence of the phosphodiesters in the strand

 

  1. E)

 

the sequence of the 5′-OH groups in the strand

 

Answer:
 

A

 

Section:


20.2


26)
 

Which of the following statements is not true about the structure of DNA as proposed by Watson and Crick?

 

  1. A)

 

The number of adenines in DNA is equal to the number of thymines.

 

  1. B)

 

The number of cytosines is equal to the number of guanines.

 

  1. C)

 

DNA consists of two strands of nucleic acids with the sugar-phosphate backbone on the inside and the bases on the outside.

 

  1. D)

 

The chains in DNA are held together by hydrogen bonding.

 

  1. E)

 

Adenine always pairs with thymine and guanine always pairs with cytosine.

 

Answer:
 

C

 

Section:


20.2


27)
 

How many hydrogen bonds exist between the cytosine/guanine base pairs?

 

  1. A)

 

1

 

  1. B)

 

2

 

  1. C)

 

3

 

  1. D)

 

4

 

  1. E)

 

5

 

Answer:
 

C

 

Section:


20.2


28)
 

Which of the following is the conventional method of writing the base sequence of a portion of a DNA chain?

 

  1. A)

 

5′-end–bases–5′-end

 

  1. B)

 

5′-end–bases–3′-end

 

  1. C)

 

3′-end–bases–5′-end

 

  1. D)

 

3′-end–bases–3′-end

 

  1. E)

 

5′-end–bases–2′-end

 

Answer:
 

B

 

Section:


20.2


29)
 

What are stacking interactions in DNA and what purpose do they serve?

 

Answer:
 

Stacking interactions are weak attractive forces (van der Waal’s forces) that contribute significantly to the stability of the double helix. Stacking interactions are strongest between two purines and weakest between two pyrimidines.

 

Section:


20.2


30)
 

Show the hydrogen bonding which occurs when guanine and cytosine form a base pair.

 

Answer:
 

 

 

 

Section:


20.2


31)
 

Show the hydrogen bonding which occurs when adenine and thymine form a base pair.

 

Answer:
 

 

 

 

Section:


20.2


32)
 

What is the sequence of bases in the strand of DNA that is complementary to that shown below?

5′-T-T-C-A-C-T-G-A-C-3′

 

  1. A)

 

5′-T-T-C-A-C-T-G-A-C-3′

 

  1. B)

 

3′-T-T-C-A-C-T-G-A-C-5′

 

  1. C)

 

5′-A-A-G-T-G-A-C-T-G-3′

 

  1. D)

 

5′-G-T-C-A-G-T-G-A-A-3′

 

  1. E)

 

3′-U-U-C-A-C-U-G-A-C-5′

 

Answer:
 

C

 

Section:


20.2


33)
 

Explain why RNA is easily cleaved and DNA is not.

 

Answer:
 

RNA can be easily cleaved because the 2′-OH group of ribose is the nucleophile that cleaves the RNA strand. DNA does not have a 2′-OH group.

 

Section:


20.3


34)
 

What is meant by semiconservative DNA replication?

 

Answer:
 

When DNA strands are replicated, two daughter molecules of DNA are produced. Each daughter molecule contains one of two original strands plus a newly synthesized strand. This is called semiconservative DNA replication.

 

Section:


20.4


35)
 

Genes are segments of DNA.

 

Answer:
 

TRUE

 

Section:


20.4


36)
 

What is the direction that a nucleic acid must be synthesized?

 

Answer:
 

From the 5′ to the 3′ direction.

 

Section:


20.4


37)
 

How many billion base pairs are there in the total DNA of a human cell?

 

  1. A)

 

3

 

  1. B)

 

5

 

  1. C)

 

8

 

  1. D)

 

11

 

  1. E)

 

13

 

Answer:
 

A

 

Section:


20.5


38)
 

Define “transcription.”

 

Answer:
 

The synthesis of RNA from a DNA blueprint.

 

Section:


20.5


39)
 

In an entire DNA strand, what percentage consists of genetic information and what percentage consists of introns?

 

  1. A)

 

98% genetic information, 2% introns

 

  1. B)

 

2% genetic information, 98% introns

 

  1. C)

 

50% genetic information, 50% introns

 

  1. D)

 

100% genetic information, 0% introns

 

  1. E)

 

99% genetic information, 1% introns

 

Answer:
 

B

 

Section:


20.5


40)
 

Which of the following statements best describes the meaning of transcription?

 

  1. A)

 

the synthesis of rRNA from a DNA blueprint

 

  1. B)

 

Transcription is synonymous with replication.

 

  1. C)

 

the synthesis of identical copies from a DNA blueprint

 

  1. D)

 

the synthesis of mRNA from a DNA blueprint

 

  1. E)

 

the synthesis of tRNA from a DNA blueprint

 

Answer:
 

D

 

Section:


20.5


41)
 

Define “translation.”

 

Answer:
 

The synthesis of proteins from a RNA blueprint.

 

Section:


20.5


42)
 

Which of the following statements concerning nucleic acids is not correct?

 

  1. A)

 

The enzymes that catalyze DNA synthesis are known as DNA polymerases.

 

  1. B)

 

The growing DNA polymer is synthesized in the 5′ to 3′ direction.

 

  1. C)

 

RNA strands are synthesized in the 3′ to 5′ direction.

 

  1. D)

 

In DNA the distance between the strands of the double helix is relatively constant.

 

  1. E)

 

Unlike DNA, RNA is easily cleaved because the 2′-OH group of the ribose can act as the nucleophile that cleaves the strand.

 

Answer:
 

C

 

Section:


20.6


43)
 

Which of the following statements is not true about RNA?

 

  1. A)

 

It is single stranded.

 

  1. B)

 

It is smaller than DNA.

 

  1. C)

 

It has fewer base pairs than DNA.

 

  1. D)

 

It exists exclusively in the nucleus of the cell.

 

  1. E)

 

There are three kinds: rRNA, mRNA, and tRNA.

 

Answer:
 

D

 

Section:


20.6


44)
 

Which of the following is true about tRNA?

 

  1. A)

 

All tRNA’s have a CCG sequence at the 3′-end.

 

  1. B)

 

All tRNA’s have a CCG sequence at the 5′-end.

 

  1. C)

 

All tRNA’s have a CCA sequence at the 5′-end.

 

  1. D)

 

All tRNA’s have a CCA sequence at the 3′-end.

 

  1. E)

 

All tRNA’s have a CAC sequence at the 3′-end.

 

Answer:
 

D

 

Section:


20.7


45)
 

Which of the following is the sequence of bases that determines the sequence of amino acids in a protein?

 

  1. A)

 

DNA

 

  1. B)

 

messenger RNA

 

  1. C)

 

ribosomal RNA

 

  1. D)

 

transfer RNA

 

  1. E)

 

transcription DNA

 

Answer:
 

B

 

Section:


20.7


46)
 

Which is a structural component of ribosomes, which are the particles on which the biosynthesis of proteins take place?

 

  1. A)

 

DNA

 

  1. B)

 

messenger RNA

 

  1. C)

 

ribosomal RNA

 

  1. D)

 

transfer RNA

 

  1. E)

 

transcription DNA

 

Answer:
 

C

 

Section:


20.7


47)
 

What is the carrier of amino acids for protein synthesis?

 

  1. A)

 

DNA

 

  1. B)

 

messenger RNA

 

  1. C)

 

ribosomal RNA

 

  1. D)

 

transfer RNA

 

  1. E)

 

transcription DNA

 

Answer:
 

D

 

Section:


20.7


48)
 

What is a codon? Give an example.

 

Answer:
 

A codon is a sequence of three bases that specifies a particular amino acid that is to be incorporated into a protein.

 

Ex. CUU is the code for leucine.

 

Section:


20.8


49)
 

Methionine is the first amino acid incorporated into the heptapeptide specified by the following mRNA:

5’AUGGACCCCGUUAUUAAACAC-3′. What is the sequence of the amino acid in the heptapeptide?

 

Answer:
 

Using the genetic code table, the sequence is Met-Asp-Pro-Val-Ile-Lys-His.

 

Section:


20.8


50)
 

Which of the following is present in DNA to prevent lethal mutations?

 

  1. A)

 

thymine

 

  1. B)

 

uracil

 

  1. C)

 

mycin

 

  1. D)

 

amphenicol

 

Answer:
 

A

 

Section:


20.9


51)
 

Which of the following base sequences would most likely be recognized by a restriction endonuclease?

 

  1. A)

 

ACGCGT

 

  1. B)

 

ACGGGT

 

  1. C)

 

ACACGT

 

  1. D)

 

ACATCGT

 

  1. E)

 

CCAACC

 

Answer:
 

A

 

Section:


20.10


52)
 

What are Maxam-Gilbert and Sanger sequencing?

 

Answer:
 

They are methods used to sequence restriction fragments of DNA.

 

Section:


20.10


53)
 

What technique has made DNA analysis a much faster process than when it was first developed?

 

Answer:
 

PCR (polymerase chain reaction)

 

Section:


20.11

 


 

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