Log out Go to App
Go to App

Learning Materials

Features

Discover

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.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Calculate \(\left[\mathrm{H}^{+}\right]\) and the \(\mathrm{pH}\) of a \(0.10 \mathrm{M}\) solution of chloroacetic acid \(\left(K_{\mathrm{a}}=1.5 \times 10^{-3}\right)\)

Write structural formulas for the following alkanes. (a) 3-ethylpentane (b) 2,2-dimethylbutane (c) 2-methyl-3-ethylheptane (d) 2,3-dimethylpentane

Write the formula for (a) an alkyne with 16 hydrogen atoms. (b) an alkene with 44 hydrogen atoms. (c) an alkane with ten carbon atoms.

Draw structures for all the saturated carboxylic acids with four carbon atoms per molecule.

In each of the following, name the functional group (i.e., ester, aldehyde, ...). (a) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{OH}\)
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Chemical Reactions

Read Explanation

The Earths Atmosphere

Read Explanation

Physical Chemistry

Read Explanation

Kinetics

Read Explanation

Making Measurements

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free