Question

Draw the structural isomers of \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{Cl}\) in which one hydrogen atom of a \(\mathrm{C}_{4} \mathrm{H}_{10}\) molecule has been replaced by chlorine.

Short answer

Question: List and draw the four possible structural isomers of C4H9Cl. Answer: The four possible structural isomers of C4H9Cl are: 1. 1-chlorobutane: Cl-CH2-CH2-CH2-CH3 2. 2-chlorobutane: CH3-CH(Cl)-CH2-CH3 3. 1-chloro-2-methylpropane: (CH3)2C(Cl)-CH3 4. 2-chloro-2-methylpropane: (CH3)3C-Cl

Step-by-step solution

Draw the isomers of C4H10

Begin by drawing the different structural isomers of C4H10, the base molecule: 1. n-butane: CH3-CH2-CH2-CH3 2. isobutane (2-methylpropane): (CH3)3C-H There are only two isomers for C4H10.

Replace a hydrogen atom with a chlorine atom in each isomer

Now, for each of the C4H10 isomers, replace one of the hydrogen atoms with a chlorine atom:

Isomer 1 – n-butane

In the case of n-butane, we can replace the hydrogens in two distinct ways: 1.1. 1-chlorobutane: Cl-CH2-CH2-CH2-CH3 1.2. 2-chlorobutane: CH3-CH(Cl)-CH2-CH3

Isomer 2 – isobutane

For isobutane, we can also replace the hydrogens in two distinct ways: 2.1. 1-chloro-2-methylpropane: (CH3)2C(Cl)-CH3 2.2. 2-chloro-2-methylpropane: (CH3)3C-Cl Therefore, there are four possible structural isomers of C4H9Cl, formed by replacing a hydrogen atom with a chlorine atom in the respective C4H10 molecule: 1. 1-chlorobutane: Cl-CH2-CH2-CH2-CH3 2. 2-chlorobutane: CH3-CH(Cl)-CH2-CH3 3. 1-chloro-2-methylpropane: (CH3)2C(Cl)-CH3 4. 2-chloro-2-methylpropane: (CH3)3C-Cl