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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

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

: Cl

: O : P Cl : : Cl : 5.
: O :
P
Cl
:
:
Cl
:
5.

6. 7.

: C
:
C

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

.

.

8.

O :
O
:

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 * CH 2 CHC O NH 3
A.
O
*
CH 2 CHC
O
NH 3

phenylalanine

B.

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

Answer:

O CH 2 CHC O NH 3
O
CH 2 CHC
O
NH 3

16. The oxygen atom labeled A. has

Answer:

four

non-bonding electrons.

17. The oxygen atom labeled B. has

Answer:

two

bonding electrons.

Use the δ /δ + convention and the crossed arrow the indicated bonds in the following compounds.

( )
(
)

18. The C F bond in fluorobenzene,

Answer:

δ−

F δ+
F
δ+
The C − F bond in fluorobenzene, Answer: δ− F δ+ F 19. The C-Si bond

F

19. The C-Si bond in tetramethylsilane, (CH 3 ) 4 Si

Answer:

H 3 C

CH 3 δ+ δ− Si CH 3
CH 3
δ+ δ−
Si
CH 3

CH 3

20. The C O bond in furan,

Answer:

O δ−
O
δ−

δ+

3 20. The C − O bond in furan, Answer: O δ− δ+ O to show

O

to show the direction of the expected polarity of

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

21.

22.

CH 3 OH Answer:

CH 3 OH

acid

CH 3 OCH 3

Answer:

CH 3 OCH 3

base

+

+

+

+

NaH

NaH

base

BH 3

BH 3

acid

CH 3 OCH 3 base + + + + NaH NaH base BH 3 BH 3

CH 3 O - Na +

+ + + + NaH NaH base BH 3 BH 3 acid CH 3 O -

CH 3 O - Na +

conjugate base

+

H 3 C O
H 3 C
O

CH 3

-

BH 3

+

H 3 C O
H 3 C
O

CH 3

-

BH 3

+

+

H 2

H 2

conjugate acid

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

pKa = 18

(CH 3 ) 3 COH

A.

+ K OH B.
+ K
OH
B.

in the blank. pKa = 18 (CH 3 ) 3 COH A. + K OH B.

(CH

O K 3 ) 3 C C.
O
K
3 ) 3 C
C.

pKa = 15.7

+

H 2

O

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 (pK a = 15.7) is a stronger acid than A (pK a = 18).

26. An acid with a low pK a :

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.

CH 3 OH

Answer:

O

bases in the group of compounds below. CH 3 OH Answer: O O CH 3 OH
O CH 3 OH
O
CH 3 OH

HCl

BCl 3

HCl

BCl 3

OH Answer: O O CH 3 OH HCl BCl 3 HCl BCl 3 N N FeBr

N

N
N

FeBr

FeBr

3

3

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

O

CH 3 OH

Answer:

acids in the group of compounds below. O CH 3 OH Answer: O CH 3 OH

O

CH 3 OH
CH 3 OH
group of compounds below. O CH 3 OH Answer: O CH 3 OH N HCl BCl

N

HCl BCl 3 HCl BCl 3
HCl
BCl 3
HCl
BCl 3

FeBr 3

3 OH Answer: O CH 3 OH N HCl BCl 3 HCl BCl 3 FeBr 3

N

FeBr 3 + O
FeBr 3
+
O

29. Draw two resonance structures for the species below.

+ O
+
O

Answer:

+ O
+
O

CH 3

CH 3

+ O
+
O

CH 3

CH 3

30. Draw two resonance structures for the species below.

Answer:

: O :

CH 2 2

_

: O : : O : CH 2 CH 2 _ _
:
O :
:
O
:
CH 2
CH 2
_
_
_ : O :
_
:
O :

CH 2

31. Draw two resonance structures for the species below.

Answer:

two resonance structures for the species below. Answer: _ O : _ _ O : O

_

O:

_

resonance structures for the species below. Answer: _ O : _ _ O : O :

_

structures for the species below. Answer: _ O : _ _ O : O : _

O:

O:

structures for the species below. Answer: _ O : _ _ O : O : _

_

O:

for the species below. Answer: _ O : _ _ O : O : _ O

_ :

for the species below. Answer: _ O : _ _ O : O : _ O

O

Consider the acidity constants below to answer the following questions.

ACID

STRUCTURE

phenol

phenol OH

OH

ethanol

CH 3 CH 2 OH

water

HOH

pK a

10.00

16.00

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 pK a ) so its conjugate base, ethoxide, CH CH O , will be the strongest base.

3

2

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

Answer:

Phenol is more acidic (has a lower pK a ) 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.

stabilization. The negative charge is borne fully by oxygen. OH CH 3 CH 2 OH -H

OH

CH 3 CH 2 OH

-H + -H +

_

CH 3 CH 2 O :

-H +

CH 2 OH -H + _ C H 3 C H 2 O : -H +

O: :

_

O: :

_

_

O: _ : O
O:
_ :
O

Test Items for McMurry’s Organic Chemistry, Seventh Edition

9

Consider the reaction below to answer the following questions.

H

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

H

H

+ H

O

O : :

below to answer the following questions. H H H + H O O : H H

H

H

to answer the following questions. H H H + H O O : H H H

H

H

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

Answer:

H

H + H
H
+ H

H

O N O +
O
N
O
+

O :

for this reaction. Answer: H H + H H O N O + O : H

H

H

Hfor this reaction. Answer: H H + H H O N O + O : H

H

O _ N O + O O _ N O + O
O
_
N
O
+
O
O
_
N
O
+
O

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

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

H

H

+ N
+
N

H

H

O _ N O + O
O
_
N
O
+
O

_

_

_

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.

N H
N
H

indole

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:

10

N H
N
H
that demonstrates this reactivity of indole. Answer: 10 N H B N + BH Chapter 2:

B

N
N

+

BH

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 N H
H
A
N
H
N H H
N
H
H
this reactivity of indole. Answer: H A N H N H H + A 39. The

+ A

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.

Answer:

CH 3 OCH 3

dimethyl ether

net dipole

O H 3 C CH 3
O
H 3 C
CH 3

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

CH 3 CH O CH 3
CH 3 CH
O
CH 3

base

+

HOH

acid

the following questions. CH 3 CH O CH 3 base + HOH acid 40. Using the

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

Answer:

O + HOH CH 3 CH CH 3 base acid
O
+
HOH
CH 3 CH
CH 3
base
acid

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

Answer:

CH 3 CH O CH 3
CH 3 CH
O
CH 3

base

+ HOH

acid

CH 3 CH O CH 3
CH 3 CH
O
CH 3

H

+

Test Items for McMurry’s Organic Chemistry, Seventh Edition

O
O

H

11