Advanced Chemistry: Alkanes & Cycloalkanes Name:

1. Write the structural formulas for each of the following. For those with common names, rename them by IUPAC

a. 2,3-Dichloropentane

b. tert-Butyl iodide

c. 3-Ethylpentane

d. 2,3,4-Trimethyldecane

e. 4-Isopropylnonane

f. neo-Pentyl chloride

g. iso-Butyl alcohol

h. 1,1-Dimethylcyclopropane

i. cis-1,2-Dimethylcyclobutane

j. trans-1-ethyl-3-methylcyclohexane

k. iso-hexyl chloride

2. Write the structures of two chair conformations of 1-tert-butyl-1-methylcyclohexane. Which conformation

would you predict as the most stable?

3. Consider each pair of structural formulas and state whether they are the same or different compounds

a. CH₃ and H H H

| | | |

CH₂—CH₂ H—C—C—C—Br

| | | |

Br H H H

b. CH₃CH₂CH₂ and ClCH₂CH(CH₃)₂

|

CH₂—Cl

c. H H

| |

Cl—C—Cl and H—C—Cl

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H Cl

O

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d. CH₃OCH₂CH₃ and CH₃—C—CH₃