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Chapter 22: Problem 36

Write structures for all the structural isomers of compounds with the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{ClBr}\) in which \(\mathrm{Cl}\) and \(\mathrm{Br}\) are bonded to a doublebonded carbon.

Short Answer

Expert verified
There are 6 structural isomers of compounds with molecular formula \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{ClBr}\) that have chlorine and bromine bonded to a double-bonded carbon atom.

Step by step solution

01

Identify the Base Structure

Let's start with the arrangement of the carbon atoms. A molecular formula of \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{ClBr}\) implies that there's a double bond, as deduced by the degree of unsaturation from the formula: Degree of Unsaturation = \(\frac{2 \times n + 2 - X}{2}\), where n is the number of carbon atoms, and X is the number of hydrogen, halogen atoms. Degree of Unsaturation = \(\frac{2 \times 4 + 2 - 6 - 1 - 1}{2} = 1\) Since there's only one degree of unsaturation, we will form only one double bond in the molecules.
02

Determine Position of Double Bond

Now, we'll determine the possible positions for the double bond across the four carbon atoms. There are three possibilities for the double bond, which are: 1. Carbon 1 and Carbon 2 2. Carbon 2 and Carbon 3 3. Carbon 3 and Carbon 4
03

Attach Chlorine and Bromine

Next, we'll attach the chlorine and bromine atoms to the double-bonded carbon atoms as per the given condition. It can be done in two ways: 1. Chlorine attached to first double-bonded carbon and bromine attached to the second double-bonded carbon 2. Bromine attached to first double-bonded carbon and chlorine attached to the second double-bonded carbon
04

Combine Double Bonds and Halogen Positions

For the three double bond possibilities, let's have each possible arrangement of chlorine and bromine: 1. Double bond between Carbon 1 and Carbon 2 - Chlorine attached to Carbon 1, Bromine attached to Carbon 2 - Bromine attached to Carbon 1, Chlorine attached to Carbon 2 2. Double bond between Carbon 2 and Carbon 3 - Chlorine attached to Carbon 2, Bromine attached to Carbon 3 - Bromine attached to Carbon 2, Chlorine attached to Carbon 3 3. Double bond between Carbon 3 and Carbon 4 - Chlorine attached to Carbon 3, Bromine attached to Carbon 4 - Bromine attached to Carbon 3, Chlorine attached to Carbon 4
05

Draw Structures

Now that we have all possible combinations, let's draw them: 1.1. \(\ce{C(Cl)=C(Br)-CH2-CH3}\) 1.2. \(\ce{C(Br)=C(Cl)-CH2-CH3}\) 2.1. \(\ce{CH2-C(Cl)=C(Br)-CH3}\) 2.2. \(\ce{CH2-C(Br)=C(Cl)-CH3}\) 3.1. \(\ce{CH3-CH2-C(Cl)=C(Br)}\) 3.2. \(\ce{CH3-CH2-C(Br)=C(Cl)}\) These six structures represent all the structural isomers of compounds with molecular formula \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{ClBr}\) that have chlorine and bromine bonded to a double-bonded carbon atom.

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