Explain why each is an incorrect IUPAC name, and write the correct IUPAC name for the intended compound. (a) 1,3-Dimethylbutane (b) 4 -Methylpentane (c) 2,2-Diethylbutane (d) 2-Ethyl-3-methylpentane (e) 2-Propylpentane (f) 2,2-Diethylheptane (g) 2,2-Dimethylcyclopropane (h) 1-Ethyl-5-methylcyclohexane

Short Answer

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(a) 1,3-Dimethylbutane (b) 4-Methylpentane (c) 2,2-Diethylbutane (d) 2-Ethyl-3-methylpentane (e) 2-Propylpentane (f) 2,2-Diethylheptane (g) 2,2-Dimethylcyclopropane (h) 1-Ethyl-5-methylcyclohexane Answer: The compounds with incorrect IUPAC names and their correct names are: (a) 1,3-Dimethylbutane - Correct name: 2,3-Dimethylbutane (b) 4-Methylpentane - Correct name: 2-Methylpentane (c) 2,2-Diethylbutane - Correct name: 3-Ethylpentane (if the intended compound has one ethyl substituent) (e) 2-Propylpentane - Correct name: 4-Methylheptane (f) 2,2-Diethylheptane - Correct name: 4,4-Diethylheptane (if the intended compound has two ethyl substituents) (g) 2,2-Dimethylcyclopropane - Correct name: 1,1-Dimethylcyclopropane (h) 1-Ethyl-5-methylcyclohexane - Correct name: 1-Ethyl-3-methylcyclohexane

Step by step solution

01

(a) 1,3-Dimethylbutane

This name is incorrect because there is no need to specify the positions of methyl groups since they are at the ends of the chain, we should also change the numbering to have the lower numbers. The correct IUPAC name for this compound is 2,3-Dimethylbutane.
02

(b) 4-Methylpentane

This name is incorrect because the position of the methyl group should be at the lowest numbered carbon atom in the chain. The correct IUPAC name for this compound is 2-Methylpentane.
03

(c) 2,2-Diethylbutane

This name is incorrect because there is no isomer with two ethyl substituents at the same carbon atom of a butane molecule. The correct name based on the intended compound might be 3-Ethylpentane.
04

(d) 2-Ethyl-3-methylpentane

This name is correct as per IUPAC nomenclature rules, so no changes are needed.
05

(e) 2-Propylpentane

This name is incorrect because the chain with the propyl group attached should be considered the main chain. The correct IUPAC name for this compound is 4-Methylheptane.
06

(f) 2,2-Diethylheptane

This name is incorrect because there is no isomer with two ethyl substituents at the same carbon atom of a heptane molecule. The correct name based on the intended compound might be 4,4-Diethylheptane.
07

(g) 2,2-Dimethylcyclopropane

This name is incorrect because there is only one possible position for methyl substituents in a cyclopropane molecule. The correct IUPAC name for this compound is 1,1-Dimethylcyclopropane.
08

(h) 1-Ethyl-5-methylcyclohexane

This name is incorrect because the compound should be numbered to give the substituents the lowest possible numbers. The correct IUPAC name for this compound is 1-Ethyl-3-methylcyclohexane.

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Most popular questions from this chapter

Using a planar pentagon representation for the cyclopentane ring, draw structural formulas for the cis and trans isomers of the following. (a) 1,2-Dimethylcyclopentane (b) 1,3-Dimethylcyclopentane

From studies of the dipole moment of 1,2 -dichloroethane in the gas phase at room temperature \(\left(25^{\circ} \mathrm{C}\right)\), it is estimated that the ratio of molecules in the anti conformation to gauche conformation is \(7.6\) to 1 . Calculate the difference in Gibbs free energy between these two conformations.

Without consulting tables, arrange these compounds in order of decreasing (less negative) heat of combustion: hexane, 2-methylpentane, and 2 ,2-dimethylbutane.

Each member of the following set of compounds is an alcohol; that is, each contains an -OH (hydroxyl group, Section 1.3A). Which structural formulas represent the same compound, and which represent constitutional isomers? (a) CCC(C)O (b) OC1CCC1 (c) OCC1CC1 (d) CC(C)CO (e) CC(C)CO (f) CCCCO \((\mathrm{g})\) CCC(C)O (h) CC1(O)CCCCC1

Consider 1-bromopropane, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\). (a) Draw a Newman projection for the conformation in which \(-\mathrm{CH}_{3}\) and \(-\mathrm{Br}\) are anti (dihedral angle \(180^{\circ}\) ). (b) Draw Newman projections for the conformations in which \(-\mathrm{CH}_{3}\) and \(-\mathrm{Br}\) are gauche (dihedral angles \(60^{\circ}\) and \(300^{\circ}\) ). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?

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