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Chapter 17: Problem 121

There are four isomers that have the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{9}\) Br. Draw the structural formula for each one. Name each compound using IUPAC rules.

Short Answer

Expert verified
The four isomers with the molecular formula C4H9Br are: 1. 1-bromobutane: Br-CH2-CH2-CH2-CH3 2. 2-bromobutane: CH3-CH(Br)-CH2-CH3 3. 1-bromo-2-methylpropane: Br-CH(CH3)-CH2-CH3 4. 2-bromo-2-methylpropane: CH3-C(Br)(CH3)-CH3

Step by step solution

01

Identify the possible carbon chain configurations

We have four carbons in the molecule, so we will have two possible carbon chain configurations: a straight chain with 4 carbons, and a branched chain with three carbons and one branch.
02

Determine the isomers

For each carbon chain configuration, we can add the bromine atom at different positions. This will give us four isomers in total.
03

Draw the structural formulas

Now let's draw the structural formulas for each isomer. 1. 1-bromobutane: Straight chain with 4 carbons Bromine atom is on the first carbon. Structure: Br-CH2-CH2-CH2-CH3 2. 2-bromobutane: Straight chain with 4 carbons Bromine atom is on the second carbon. Structure: CH3-CH(Br)-CH2-CH3 3. 1-bromo-2-methylpropane: Branched chain with 3 carbons and one branch (methyl) Bromine atom is on the first carbon. Structure: Br-CH(CH3)-CH2-CH3 4. 2-bromo-2- methylpropane: Branched chain with 3 carbons and one branch (methyl) Bromine atom is on the second carbon with the methyl group. Structure: CH3-C(Br)(CH3)-CH3
04

Name the compounds

We will use IUPAC nomenclature to name each compound. 1. 1-bromobutane 2. 2-bromobutane 3. 1-bromo-2-methylpropane 4. 2-bromo-2-methylpropane

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Most popular questions from this chapter

The IUPAC name for \(\mathrm{C}_{3} \mathrm{H}_{6}\) needs no number in it, but the IUPAC name for \(\mathrm{C}_{4} \mathrm{H}_{8}\) does. Explain.

Although it was not discussed in the chapter, it is possible for a hydrocarbon molecule to have more than one site of unsaturation. One such molecule is 1,3 -butadiene; the \(d i\) - tells us there are two double bonds in the molecule. Give the molecular formula and line drawing for this molecule.

(a) What functional group does the molecule ethanal contain? How can you tell? (b) Draw a dot diagram for the molecule. Answer: (a) The ending -al tells you this molecule is an aldehyde. It therefore contains the aldehyde functional group.

Show how a carboxylic acid, \(\mathrm{R}-\mathrm{COOH}\), reacts with a tertiary amine, \(\mathrm{NR}_{3}\).

Explain how hydrocarbons containing an OH group are named.
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