Using the general molecular formula for alkanes:

a. Predict the molecular formula of the C₂₈ straight-chain alkane.

Name the following alkanes and haloalkanes. When two or more substituents are present, list them in alphabetical order.

(a)

Name the following alkanes and haloalkanes. When two or more substituents are present, list them in alphabetical order.

(b)

Name the following alkanes and haloalkanes. When two or more substituents are present, list them in alphabetical order.

(c)

(d)

Write structures for the following compounds.

a. 3-ethyl-4-methylhexane

b. 3-ethyl-5-isobutyl-3-methylnonane

c. 4-tert-butyl-2-methylheptane

d. 5-isopropyl-3,3,4-trimethyloctane

Provide IUPAC names for the following compounds.

a. (CH₃)₂CHCH₂CH₃

b. CH₃—C(CH₃)₂—CH₃

c.

Provide IUPAC names for the following compounds.

(d)

(e)

(f)

All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly.

a. 3-ethyl-4-methylpentane

b. 2-ethyl-3-methylpentane

c. 3-dimethylhexane

All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly.

d. 4-isobutylheptane

e. 2-bromo-3-ethylbutane

f. 2,3-diethyl-5-isopropylheptane

Give structures and names for

a. the five isomers of C₆H₁₄

Draw the structures of the following groups, and give their more common names.

a. the (1-methylethyl) group

b. the (2-methylpropyl) group

c. the (1-methylpropyl) group

d. the (1,1-dimethylethyl) group

e. the (3-methylbutyl) group, sometimes called the 'isoamyl' group

Draw the structures of the following compounds.

a. 4-(1,1-dimethylethyl)octane

Draw the structures of the following compounds.

b. 5-(1,2,2-trimethylpropyl)nonane

Draw the structures of the following compounds.

c. 3,3-diethyl-4-(2,2-dimethylpropyl)octane

Without looking at the structures, give molecular formulas for the compounds: (a) 4-(1,1-dimethylethyl)octane and (b) 5-(1,2,2-trimethylpropyl)nonane. Use the names of the groups to determine the number of carbon atoms; then use the (2n + 2) rule.

List each set of compounds in order of increasing boiling point.

a. hexane, octane, and decane

List each set of compounds in order of increasing boiling point.

b. Octane, (CH₃)₃C—C(CH₃)₃ and CH₃CH₂C(CH₃)₂CH₂CH₂CH₃

Draw Newman projections of the following molecules viewed from the direction of the blue arrows.

(a)

Draw Newman projections of the following molecules viewed from the direction of the blue arrows.

(b)

Draw Newman projections of the following molecules viewed from the direction of the blue arrows.

(c)

Draw a graph, similar to Figure 3-9, of the torsional strain of 2-methylpropane as it rotates about the bond between C1 and C2. Show the dihedral angle and draw a Newman projection for each staggered and eclipsed conformation.

Draw a graph, similar to Figure 3-11, of the torsional energy of 2-methylbutane as it rotates about the C2—C3 bond.

Draw a perspective representation of the most stable conformation of 3-methylhexane.

Give IUPAC names for the following compounds.

Draw the structure and give the molecular formula for each of the following compounds.

a. 1-ethyl-3-methylcycloheptane

b. isobutylcyclohexane

Draw the structure and give the molecular formula for each of the following compounds.

c. cyclopropylcyclopentane

d. 3-ethyl-1,1-dimethylcyclohexane

Draw the structure and give the molecular formula for each of the following compounds.

e. 3-ethyl-2,4-dimethylhexane

f. 1,1-diethyl-4-(3,3-dimethylbutyl)cyclohexane