Chapter 2 - Polar Covalent Bonds; Acids and Bases

For questions 1-10 give the letter of the term that best matches the given definition.

a. Brønsted-Lowry Acid f. Ionic Bond

b. Brønsted-Lowry Base g. Covalent Bond
c. Lewis Acid h. Polar-Covalent Bond
d. Lewis Base i. Hydrophobic
e. Electronegativity j. Hydrophilic

1. Any species that can accept electrons.

Answer: c

2. A bond between two atoms differing in electronegativity by 0.5 – 2.

Answer: h

3. A term used to describe a “water loving” species.

Answer: j

4. A compound that can donate a proton.

Answer: a

5. The ability of an atom to attract the shared electrons in a covalent bond.

Answer: e

6. A term used to describe a “water fearing” species.

Answer: i

7. Any species that can donate electrons.

Answer: d

8. A bond between two atoms differing in electronegativity by < 0.5

Answer: g

9. A compound that can accept a proton.

Answer: b

10. A bond between two atoms differing in electronegativity by > 2.

Answer: f

4 Chapter 2: Polar Covalent Bonds; Acids and Bases

Calculate the formal charges on the indicated atoms in each compound below.

..
:O : 6. 7. 8.
.. ..
:Cl P Cl :
.. .. :C O:
: Cl : 5.
..

11. The formal charge on phosphorous is .

Answer: +1

12. The formal charge on oxygen is .

Answer: –1

13. The formal charge on carbon is .

Answer: –1

14. The formal charge on oxygen is .

Answer: +1

Phenylalanine is an amino acid that is essential to human nutrition. The representation below shows the
structure of phenylalanine at physiological pH. Consider this structure to answer the following questions.
A.
O
*
CH2CHC O phenylalanine
NH3 B.

15. Assign any formal charges to atoms in this representation of phenylalanine.

Answer:
O
CH2CHC O
NH3

16. The oxygen atom labeled A. has ______ non-bonding electrons.

Answer: four

17. The oxygen atom labeled B. has _____ bonding electrons.

Answer: two

Test Items for McMurry’s Organic Chemistry, Seventh Edition 5

Use the δ − /δ + convention and the crossed arrow ( ) to show the direction of the expected polarity of
the indicated bonds in the following compounds.

F
18. The C − F bond in fluorobenzene,

δ−
δ+ F
Answer:

19. The C-Si bond in tetramethylsilane, (CH3)4Si

CH3
δ+ δ−
Answer: H3C Si CH3

CH3

20. The C − O bond in furan,

O

Answer:
δ+
δ−O

Label the acid, conjugate acid, base, and conjugate base in each reaction below.

21. CH3OH + NaH CH3O- Na+ + H2

Answer:

CH3OH + NaH CH3O- Na+ + H2

acid base conjugate base conjugate acid

+ -
22. CH3OCH3 + BH3 H3C O BH3

CH3
Answer:
+ -
CH3OCH3 + BH3 H3C O BH3
base acid CH3

6 Chapter 2: Polar Covalent Bonds; Acids and Bases

Refer to the following equation to answer the questions below. Place the letter corresponding to the correct
answer in the blank.

pKa = 18 pKa = 15.7

(CH3)3C O H + K OH (CH3)3C O K + H2O
A. B. C. D.

23. The strongest Brønsted-Lowry acid in the equation is .

Answer: D

24. The strongest Brønsted-Lowry base in the equation is .

Answer: C

25. Will this reaction take place as written? Explain.

Answer: No, the reaction will not take place as written because the strongest acid reacts with the
strongest base to give the weakest conjugate acid and the weakest conjugate base. D (pKa =
15.7) is a stronger acid than A (pKa = 18).

26. An acid with a low pKa:

a. is a weak acid
b. is a strong acid
c. has a weak conjugate base
d. both b and c

Answer: d

27. Circle all the Lewis bases in the group of compounds below.

CH3 OH HCl BCl3 FeBr3

Answer:
O

CH3 OH HCl BCl3 FeBr3

Test Items for McMurry’s Organic Chemistry, Seventh Edition 7

28. Put a box around all the Lewis acids in the group of compounds below.
O

CH3 OH HCl BCl3 FeBr3

N
Answer:

CH3 OH HCl BCl3 FeBr3

29. Draw two resonance structures for the species below.

+ .. CH3
O
..

Answer:

+ CH3 + .. CH3
.. CH3 +
O O O
.. ..

30. Draw two resonance structures for the species below.

:O :

_CH
.. 2

Answer:
.. _
:O : :O : :O :

_CH
.. 2 ..
_ CH2 CH2

31. Draw two resonance structures for the species below.

_
..

O:
..

Answer:
_
..
.. _ .. _: ..
O : O: O: O
.. .. ..
_..

8 Chapter 2: Polar Covalent Bonds; Acids and Bases

Consider the acidity constants below to answer the following questions.

ACID STRUCTURE pKa

phenol OH 10.00

ethanol CH3CH2OH 16.00

water HOH 15.74

32. Which acid above will be almost completely deprotonated by NaOH?

Answer: phenol

33. Which acid has the strongest conjugate base?

Answer: Ethanol is the weakest acid (largest pKa) so its conjugate base, ethoxide, CH 3CH 2O − , will be
the strongest base.

34. Explain why phenol has a much lower pKa than ethanol.

Answer: Phenol is more acidic (has a lower pKa) than ethanol because the phenoxide anion is resonance
stabilized by the pi electrons in the ring.

Ethoxide anion has no resonance stabilization. The negative charge is borne fully by oxygen.

-H+ .. _
CH3CH2OH CH3CH2O :
..

_
..
.. -H+ .. _
OH
.. O : O :
.. ..

.. ..
O: _: O
..
_..

Test Items for McMurry’s Organic Chemistry, Seventh Edition 9

Consider the reaction below to answer the following questions.
O O
H
N .. _ _ N _
H N H + H O + O: +
H N H O + O
..
H H

35. Using the curved arrow formalism, show the flow of electrons for this reaction.

Answer:
O O
H
N .. _ _ N _
H N H + H O + O:
.. H +N H O + O
H H

36. Label the acid and the base in the reaction.

Answer:
O O
H
N .. _ _ N _
H N H + H O + O: +
H N H O + O
..
H H
base acid

Indole is pleasant smelling in highly dilute solutions and had been used in perfumery. Use the structure of
indole, below, to answer the following questions.

indole
N
H

37. Indole can function as a Bronsted-Lowry acid in the presence of strong bases. Formulate a reaction,
showing electron flow with arrows, that demonstrates this reactivity of indole.

Answer:

B + BH
N N
H

10 Chapter 2: Polar Covalent Bonds; Acids and Bases

38. Indole can function as a Lewis base in the presence of strong acid. Formulate a reaction, showing electron
flow with arrows, that demonstrates this reactivity of indole.

Answer:

H A + A
N N
H
H
H
39. The condensed structure for dimethyl ether looks symmetrical. However, dimethyl ether has a dipole
moment. Draw a structure that explains this and indicate the expected direction of the molecular dipole
moment.
CH3OCH3

dimethyl ether
Answer:

net dipole

H3C CH3

Consider the acid-base reaction below to answer the following questions.

CH3CH O + H O H

CH3
base acid

40. Using the curved arrow formalism, show the flow of electrons for this reaction.

Answer:

CH3CH O + H O H

CH3
base acid

41. Write the products of this Lewis acid - base reaction.

Answer:
CH3CH O + H O H CH3CH O H + O H

CH3 CH3
base acid

Test Items for McMurry’s Organic Chemistry, Seventh Edition 11