Chapter 3

Draw structural formulas corresponding to the following names: a. \(2,7,8\) -trimethyldecane b. \(2,3,4\) -trimethyl-4-propylheptane c. 5 -(1,1-dimethylpropyl)nonane d. 4 -(chloromethyl)-5-(1-nitroethyl)decane

Give the IUPAC name for each of the following structures: a. \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}\left(\mathrm{CH}_{2} \mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) ?. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\) d. \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\)

The following are improper IUPAC names. Determine what is incorrect or ambiguous about the name and give the correct name. a. 2 -methyl-3-propylpentane b. 3-methyl-3-chloropentane c. \(2,3,3,7,7\) -pentamethyloctane d. 3-(1,1-dimethylethyl)pentane

Write structural formulas for each of the following: a. (2,2-dimethylpropyl)cyclopentane b. 1,2,3-tri(chloromethyl) cyclopropane c. 1,4 -dicyclohexylcyclooctane d. 1-(1-methylcyclopropyl)-1,2,2,3,3-pentamethylcyclopropane

Write structural formulas corresponding to the following IUPAC names: a. \(1,3,6\) -trimethylcyclohexene b. 1,2,3,3-tetrachlorocyclopropene c. 2,5-dimethyl-1,5-hexadiene d. 3-methylidenecyclohexane

Draw structures for the following compounds: a. 1,3 -hexadien-5-yne b. 1 -cyclodecen-4-yne c. 5-ethynyl-1,3,6-heptatriene d. 3-methylidenecyclooctyne

There are nine heptane isomers of formula \(\mathrm{C}_{7} \mathrm{H}_{16}\). Write structural formulas for each. Name each by the IUPAC system.

Write structural formulas for the eight position isomers of \(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{Cl}\). Name each as a chloroalkane.

Draw the structure of 1,1-dimethyl-3-(1-methyethyl)cyclohexane four times. In the first structure circle all the primary carbons; in the second, circle all the secondary carbons; in the third, circle the tertiary carbons; in the fourth, circle the quaternary carbons.

Draw the possible primary alkyl or alkenyl groups of formulas: a. \(\mathrm{C}_{5} \mathrm{H}_{11}\) (four) b. \(\mathrm{C}_{5} \mathrm{H}_{9}\) (eight)

Write structural formulas for the following substituent groups: a. chloromethyl b. 1 -chloroethyl c. 3 -methylbutyl d. 1,2-dimethylpropyl e. 1 -methyl-2-propenyl f. 2-methyl-1-propenyl g. 1 -buten-3-ynyl h. 2 -methylcyclohexyl i. 2 -cyclohexenyl j. phenylmethyl k. para-nitrophenyl 1\. 2,4 -dichlorophenyl m. propylidene

Name the following substituent groups by the IUPAC system and indicate whether they are primary, secondary, tertiary, or aryl groups: a. \(\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2}-\) b. \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2}\right)_{3} \mathrm{C}-\) c. \(\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CCH}_{2}-\)

Write structural formulas for each of the following substances: a. 1 -octene b. 1,4 -hexadiene c. 1,2-dimethylcyclobutane d. 1,2-cyclononadiene e. 3 -chloro-3-methyl-1-butyne f. cyclooctyne g. 2 -chloro-1,3-butadiene h. 3-methyl-2-hexen-4-yne i. (1,1-dimethylethyl)benzene j. (1-methylpropyl)benzene k. meta-nitrotoluene I. 1-phenyl-1-methylcyclohexane \(\mathbf{m}\). (phenylmethyl)cyclohexane

Name each of the following substances by the IUPAC system: a. \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{CHCH}_{3}\) b. \(\mathrm{Cl}_{2} \mathrm{C}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\) c. \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{C}=\mathrm{CHBr}\)

Decide whether the following structures are named correctly according to the IUPAC rules. If a name is incorrect or ambiguous, assign the correct name: a. 1-ethyl-2-methylbutane b. \(\mathrm{Cl}_{2} \mathrm{CHCHCl}_{2}\) tetrachloroethane C. 1-methyl-2-cyclohexene d. \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2}\) Cl 1-chloro-2-propene e. 2-ethynyl-2-butene f. phenylpropane g. dinitrobenzene h. \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{CH}_{3}\) isopentane