Chapter Questions
Draw structural formulas corresponding to the following names:a. $2,7,8$ -trimethyldecaneb. $2,3,4$ -trimethyl-4-propylheptanec. 5 -(1,1-dimethylpropyl)nonaned. 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-propylpentaneb. 3-methyl-3-chloropentanec. $2,3,3,7,7$ -pentamethyloctaned. 3-(1,1-dimethylethyl)pentane
Write structural formulas for each of the following:a. (2,2-dimethylpropyl)cyclopentaneb. 1,2,3-tri(chloromethyl) cyclopropanec. 1,4 -dicyclohexylcyclooctaned. 1-(1-methylcyclopropyl)-1,2,2,3,3-pentamethylcyclopropane
Give the IUPAC name for each of the following:
Write structural formulas corresponding to the following IUPAC names:a. $1,3,6$ -trimethylcyclohexeneb. 1,2,3,3-tetrachlorocyclopropenec. 2,5-dimethyl-1,5-hexadiened. 3-methylidenecyclohexane
Draw structures for the following compounds:a. 1,3 -hexadien-5-yneb. 1 -cyclodecen-4-ynec. 5-ethynyl-1,3,6-heptatriened. 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.
Name each of the following hydrocarbons by the IUPAC system:
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. chloromethylb. 1 -chloroethylc. 3 -methylbutyld. 1,2-dimethylpropyle. 1 -methyl-2-propenylf. 2-methyl-1-propenylg. 1 -buten-3-ynylh. 2 -methylcyclohexyli. 2 -cyclohexenylj. phenylmethylk. para-nitrophenyl1. 2,4 -dichlorophenylm. 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 -octeneb. 1,4 -hexadienec. 1,2-dimethylcyclobutaned. 1,2-cyclononadienee. 3 -chloro-3-methyl-1-butynef. cyclooctyneg. 2 -chloro-1,3-butadieneh. 3-methyl-2-hexen-4-ynei. (1,1-dimethylethyl)benzenej. (1-methylpropyl)benzenek. meta-nitrotolueneI. 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-methylbutaneb. $\mathrm{Cl}_{2} \mathrm{CHCHCl}_{2}$ tetrachloroethaneC. 1-methyl-2-cyclohexened. $\mathrm{CH}_{2}=\mathrm{CHCH}_{2}$ Cl 1-chloro-2-propenee. 2-ethynyl-2-butenef. phenylpropaneg. dinitrobenzeneh. $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{CH}_{3}$ isopentane
a. The major component in the oil obtained from pressing the rinds of oranges and lemons is a hydrocarbon called limonene. It is obtained in commercial quantities from citrus rind and is sold as a flavoring and perfume agent. Name limonene by the IUPAC system.b. The carbon skeleton of limonene is made up of branched five-carbon repeating segments called isoprene (or isoprenoid) units. Furthermore, limonene has the formula $\mathrm{C}_{10} \mathrm{H}_{16}$, which corresponds to two $\mathrm{C}_{5} \mathrm{H}_{8}$ isoprene molecules linked together.What is the IUPAC name for isoprene? Indicate the isoprene units in the limonene structure by drawing a dotted line through each of the bonds that joins one isoprene unit to the other.c. Like limonene, $\beta$ -carotene and vitamin A have carbon skeletons made up of isoprenoid units. These compounds belong to a class of naturally occurring compounds called terpenes. Mark off the isoprenoid units in $\beta$ -carotene and vitamin A as you did for limonene.
If you have access to the 1967-71 Eighth Collective Subject Index of Chemical Abstracts, locate the page number in the index where each of the compounds shown in Exercise $2-8$ occurs and give the name used. Notice that past Chemical Abstracts indexes do not use completely systematic nomenclature, especially for compounds with only a few carbons, but these indexes will be made completely systematic in the future.