Draw condensed and skeletal structures for each of the following amines:

c. 5-methyl-1-hexanamine

Draw condensed and skeletal structures for each of the following amines:

e. N,N-dimethyl-3-pentanamine

Draw condensed and skeletal structures for each of the following amines:

f. cyclohexylethylmethylamine

For each of the following, give the systematic name and the common name (if it has one) and then indicate whether it is a primary, secondary, or tertiary amine:

a.

For each of the following, give the systematic name and the common name (if it has one) and then indicate whether it is a primary, secondary, or tertiary amine:

b.

For each of the following, give the systematic name and the common name (if it has one) and then indicate whether it is a primary, secondary, or tertiary amine:

c.

For each of the following, give the systematic name and the common name (if it has one) and then indicate whether it is a primary, secondary, or tertiary amine:

d.

Predict the approximate size of the following bond angles.

(a) the C—O—C bond angle in an ether

Predict the approximate size of the following bond angles.

(b) the C—N—C bond angle in a secondary amine

Predict the approximate size of the following bond angles.

(d) the C—N—C bond angle in a quaternary ammonium salt

What is the smallest straight-chain alkane that is a liquid at room temperature (which is about 25 °C)?

Which of the following compounds forms hydrogen bonds between its molecules?

1. CH₃CH₂OCH₂CH₂OH

2. CH₃CH₂N(CH₃)₂

3. CH₃CH₂CH₂CH₂Br

Which of the preceding compounds forms hydrogen bonds with a solvent such as ethanol?

1. CH₃CH₂OCH₂CH₂OH

2. CH₃CH₂N(CH₃)₂

3. CH₃CH₂CH₂CH₂Br

Which of the preceding compounds forms hydrogen bonds with a solvent such as ethanol?

4. CH₃CH₂CH₂NHCH₃ 

5. CH₃CH₂CH₂COOH

6. CH₃CH₂CH₂CH₂F

Explain why

a. H₂O (100 °C) has a higher boiling point than CH₃OH 165 °C2.

b. H₂O (100 °C) has a higher boiling point than NH₃ (-33 °C).

Explain why

c. H₂O (100 °C) has a higher boiling point than HF 120 °C2.

d. HF 120 °C2 has a higher boiling point than NH₃ (-33 °C).

Rank the following compounds from highest boiling to lowest boiling:

In which solvent would cyclohexane have the lowest solubility: 1-pentanol, diethyl ether, ethanol, or hexane?

The effectiveness of a barbiturate as a sedative is related to its ability to penetrate the nonpolar membrane of a cell. Which of the following barbiturates would you expect to be the more effective sedative?

Draw all the staggered and eclipsed conformers that result from rotation about the C-2-C-3 bond of pentane.

Draw a potential-energy diagram for rotation about the C-2---C-3 bond of pentane through 360°, starting with the least stable conformer.

Convert the following Newman projections to skeletal structures and name them.

a.

b.

Using Newman projections, draw the most stable conformer for each of the following:

a. 3-methylpentane, viewed along the C-2---C-3 bond

Using Newman projections, draw the most stable conformer for each of the following:

b. 3-methylhexane, viewed along the C-3----C-4 bond

Using Newman projections, draw the most stable conformer for each of the following:

c. 3,3-dimethylhexane, viewed along the C-3---C-4 bond

The bond angles in a regular polygon with n sides are equal to 180° - 360°/n

a. What are the bond angles in a regular octagon?

b. What are the bond angles in a regular nonagon?

Verify the strain energy shown in Table 3.8 for cycloheptane

Draw 1,2,3,4,5,6-hexachlorocyclohexane with

a. all the chloro groups in axial positions.

b. all the chloro groups in equatorial positions.

Using the data in Table 3.9, calculate the percentage of molecules of cyclohexanol that have the OH group in an equatorial position at 25 °C.

The chair conformer of fluorocyclohexane is 0.25 kcal/mol more stable when the fluoro substituent is in an equatorial position than when it is in an axial position. How much more stable is the anti conformer than a gauche conformer of 1-fluoropropane, considering rotation about the C1−C2 bond?