Choose the more acidic member of each pair of isomers, and show why the acid you chose is more acidic.

(d)

(e)

Choose the more acidic member of each pair of isomers, and show why the acid you chose is more acidic.

(f)

(g)

Choose the more basic member of each pair of isomers, and show why the base you chose is more basic.

(a)

(b)

Choose the more basic member of each pair of isomers, and show why the base you chose is more basic.

c.

d.

Choose the more basic member of each pair of isomers, and show why the base you chose is more basic.

e.

In the following acid–base reactions,

1. draw Lewis structures of the reactants and the products.

2. determine which species are acting as electrophiles (acids) and which are acting as nucleophiles (bases).

3. use the curved-arrow formalism to show the movement of electron pairs in these ­reactions, as well as the imaginary movement in the resonance hybrids of the products.

4. indicate which reactions are best termed Brønsted–Lowry acid–base reactions.

(a)

In the following acid–base reactions,

1. draw Lewis structures of the reactants and the products.

2. determine which species are acting as electrophiles (acids) and which are acting as nucleophiles (bases).

3. use the curved-arrow formalism to show the movement of electron pairs in these ­reactions, as well as the imaginary movement in the resonance hybrids of the products.

4. indicate which reactions are best termed Brønsted–Lowry acid–base reactions.

(b)

Classify the following hydrocarbons, and draw a Lewis structure for each one. A compound may fit into more than one of the following classifications:

alkane

alkene

alkyne

cycloalkane

cycloalkene

cycloalkyne

aromatic

hydrocarbon

a. (CH₃CH₂)₂CHCH(CH₃)₂

b. CH₃CHCHCH₂CH₃

c.. CH₃CCCH₂CH₂CH₃

Classify the following hydrocarbons, and draw a Lewis structure for each one. A compound may fit into more than one of the following classifications:

alkane

alkene

alkyne

cycloalkane

cycloalkene

cycloalkyne

aromatic

hydrocarbon

(d)

(e)

(f)

Classify the following hydrocarbons, and draw a Lewis structure for each one. A compound may fit into more than one of the following classifications:

alkane

alkene

alkyne

cycloalkane

cycloalkene

cycloalkyne

aromatic

hydrocarbon

(g)

(h)

(i)

Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows:

alcohol

ether

ketone

aldehyde

carboxylic acid

alkene

(a) CH₂CHCHO

(b) CH₃CH₂CH(OH)CH₃

(c) CH₃COCH₂CH₃

Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows: alcohol ether ketone aldehyde carboxylic acid alkene

(d) CH₃CH₂OCHCH₂

(e)

Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows:

alcohol

ether

ketone

aldehyde

carboxylic acid

alkene

(f)

(g)

Draw a Lewis structure, and classify each of the following compounds. The possible classifications are as follows:

alcohol

ether

ketone

aldehyde

carboxylic acid

alkene

(h)

(i)

Draw a Lewis structure, and classify each of the following compounds:

(a) CH₃CH₂CONHCH₃

(b) (CH₃CH₂)₂NH

Draw a Lewis structure, and classify each of the following compounds:

(c) (CH₃)₂CHCOOCH₃

(d) CH₃CHCHCOCl

Draw a Lewis structure, and classify each of the following compounds:

(e) (CH₃CH₂)₂O

(f) CH₃CH₂CH₂CN

Draw a Lewis structure, and classify each of the following compounds:

(g) (CH₃)₃CCH₂CH₂COOH

(h)

Draw a Lewis structure, and classify each of the following compounds:

(i)

(j)

Draw a Lewis structure, and classify each of the following compounds:

(k)

(l)

Draw a Lewis structure, and classify each of the following compounds:

(m)

(n)

(o)

Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs.

a. CH₂=CHCH₂COOCH₃

b. CH₃OCH₃

c. CH₃CHO

Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs.

d. CH₃CONH₂

e. CH₃NHCH₃

f. RCOOH

Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs.

(g)

(h)

(i)

The C≡N triple bond in acetonitrile has a dipole moment of about 3.6 D and a bond length of about 1.16 Å. Calculate the amount of charge separation in this bond. How important is the charge-separated resonance form in the structure of acetonitrile?

For each of the following compounds,

1. draw the Lewis structure.

2. show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.

3. estimate whether the compound will have a large, small, or zero dipole moment.

a. CH₃CH=NCH₃

b. CH₃CH₂OH

c. CBr₄

For each of the following compounds,

1. draw the Lewis structure.

2. show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.

3. estimate whether the compound will have a large, small, or zero dipole moment.

d.

For each of the following compounds,

1. draw the Lewis structure.

2. show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.

3. estimate whether the compound will have a large, small, or zero dipole moment.

e.

Sulfur dioxide has a dipole moment of 1.60 D. Carbon dioxide has a dipole moment of zero, even though C―O bonds are more polar than S―O bonds. Explain this apparent contradiction.

Which of the following pure compounds can form hydrogen bonds? Which can form hydrogen bonds with water? Which ones do you expect to be soluble in water?

a. (CH₃CH₂)₂NH

b. (CH₃CH₂)₃N

c. CH₃CH₂CH₂OH

d. (CH₃CH₂CH₂)₂OH