4. Alkanes and Cycloalkanes

Draw the structures and provide systematic names for parts a, b, and c by substituting a chlorine for a hydrogen of methylcyclohexane:

(c) three secondary alkyl halides

Draw the structures and provide systematic names for parts a, b, and c by substituting a chlorine for a hydrogen of methylcyclohexane:

(b) a tertiary alkyl halide

What is each compound’s systematic name?

c.

d.

a. What is each compound’s systematic name?

b. Draw a skeletal structure for each condensed structure given and draw a condensed structure for each skeletal structure.

1. (CH₃)₃CCH₂CH₂CH₂CH(CH₃)₂

2.

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.

e. 5-(2,2-dimethylethyl)nonane

f. isopentylbromide

Name the following compounds:

e.

f.

For each of the following compounds,

1. give the IUPAC name.

2. give the common name (if possible).

3. classify the compound as a methyl, primary, secondary, or tertiary halide.

e.

For each of the following compounds,

1. give the IUPAC name.

2. give the common name (if possible).

3. classify the compound as a methyl, primary, secondary, or tertiary halide.

(f)

Draw the structures of the following compounds.

a. sec-butyl chloride

b. isobutyl bromide

For each of the following compounds,

1. give the IUPAC name.

2. give the common name (if possible).

3. classify the compound as a methyl, primary, secondary, or tertiary halide.

c.

d.

Draw all the isomers that have molecular formula C₅H₁₁Br. (Hint: There are eight.)

c. How many of the isomers are primary alkyl halides?

d. How many of the isomers are secondary alkyl halides?

e. How many of the isomers are tertiary alkyl halides?

Draw a constitutional isomer for C₄H₁₁N containing a 1° amine at a

(a) 1° carbon,

(b) 2° carbon, and

(c) 3° carbon.

Draw the structure that corresponds with each name.

k. cyclobutylcyclohexane

l. cis-1-bromo-3-chlorocyclohexane