4. Alkanes and Cycloalkanes

What is each compound's systematic name?

e.

f.

Name the following cycloalkanes using the IUPAC system of nomenclature. [Hint: Each molecule exemplifies one of the cycloalkane nomenclature rules in Table 3.10.]

(c) rule 2

Draw skeletal structures for the following:

b. 1,3-dimethylcyclohexane

Label each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).

(c) (CH₃)₂CHCH(CH₃)CH₂CH₃

(d)

Which of the following molecular formulas corresponds to a cycloalkane?

Draw and name the five cycloalkane structures of formula C₅H₁₀. Can any of these structures give rise to geometric (cis-trans) isomerism? If so, show the cis and trans stereoisomers.

Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match the description.

c. a cis-diethylcyclohexane

d. a trans-dihalocyclopentane

Draw all the isomers with molecular formula C₆H₁₂ that contain a cyclobutane ring.

Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).

c. 2-methylbutane

d. cyclohexane

Give IUPAC names for the following compounds.

Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).

e. norbornane (bicyclo[2.2.1]heptane)

trans-1,2-Dimethylcyclobutane is more stable than cis-1,2-dimethylcyclobutane, but cis-1,3-dimethylcyclobutane is more stable than trans-1,3-dimethylcyclobutane. Use drawings to explain these observations.

Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.]

(e) 2,6-diethyl-1-methylcycloheptane

Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match the description.

e. a (2,3-dimethylpentyl)cycloalkane

Name the following cycloalkanes using the IUPAC system of nomenclature. [Hint: Each molecule exemplifies one of the cycloalkane nomenclature rules in Table 3.10.]

(g) rule 4