Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 22: Problem 112

In the presence of light, chlorine can substitute for one (or more) of the hydrogens in an alkane. For the following reactions, draw the possible monochlorination products. a. 2,2 -dimethylpropane \(+\mathrm{Cl}_{2} \stackrel{\mathrm{hv}}{\longrightarrow}\) b. 1,3 -dimethylcyclobutane \(+\mathrm{Cl}_{2} \stackrel{\text { hv }}{\longrightarrow}\) c. 2,3 -dimethylbutane \(+\mathrm{Cl}_{2} \stackrel{\mathrm{hv}^{-}}{\longrightarrow}\)

Short Answer

Expert verified
a. 2,2-dimethylpropane: The monochlorination product is 2-chloro-2,2-dimethylpropane (or 1-chloro-2,2-dimethylpropane). b. 1,3-dimethylcyclobutane: The monochlorination products are 1-chloro-1,3-dimethylcyclobutane and 1-chloro-3,3-dimethylcyclobutane. c. 2,3-dimethylbutane: The monochlorination products are 1-chloro-2,3-dimethylbutane, 2-chloro-2,3-dimethylbutane (or 2-chloro-3,3-dimethylbutane), and 1-chloro-3,3-dimethylpentane.

Step by step solution

01

a. 2,2-dimethylpropane with Cl2 in the presence of light

First, draw the structure of 2,2-dimethylpropane (also known as neopentane): It has a central carbon atom bonded to three methyl groups and one hydrogen atom. All the methyl groups are identical, so there is only one type of hydrogen to be substituted. Due to the symmetry, all the methyl groups will give the same product when chlorinated. Now, draw the product formed when one H in any of the methyl groups of 2,2-dimethylpropane is replaced by a chlorine atom (Cl). You will end up with 2-chloro-2,2-dimethylpropane or 1-chloro-2,2-dimethylpropane (both names represent the same structure).
02

b. 1,3-dimethylcyclobutane with Cl2 in the presence of light

First, draw the structure of 1,3-dimethylcyclobutane: It has a cyclobutane ring with methyl groups on carbons 1 and 3. There are two types of hydrogens present: those attached to carbons 1 and 3 (secondary), and those attached to carbons 2 and 4 (primary). Now, draw two different products formed by replacing one hydrogen atom on carbon 1 or 3 with a chlorine atom, and another product formed by replacing one hydrogen atom on carbon 2 or 4 with a chlorine atom. You will have 1-chloro-1,3-dimethylcyclobutane, and 1-chloro-3,3-dimethylcyclobutane as products.
03

c. 2,3-dimethylbutane with Cl2 in the presence of light

First, draw the structure of 2,3-dimethylbutane: It has a linear carbon chain with four carbon atoms, and methyl groups are attached to carbons 2 and 3. There are three types of hydrogens present: those attached to carbon 1 (primary), those attached to carbon 4 (primary), and those attached to carbons 2 and 3 (secondary). Now, draw three different products formed by replacing one hydrogen atom on carbon 1, carbon 4, and on carbon 2 or 3 with a chlorine atom. You will have 1-chloro-2,3-dimethylbutane, 2-chloro-2,3-dimethylbutane (or 2-chloro-3,3-dimethylbutane, both names represent the same structure), and 1-chloro-3,3-dimethylpentane as products.

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

When toluene \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{3}\right)\) reacts with chlorine gas in the presence of iron(III) catalyst, the product is a mixture of the ortho and para isomers of \(\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{ClCH}_{3} .\) However, when the reaction is light-catalyzed with no \(\mathrm{Fe}^{3+}\) catalyst present, the product is \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}\). Explain.

Draw the structural formula for each of the following. a. 3 -isobutylhexane b. \(2,2,4\) -trimethylpentane, also called isooctane. This substance is the reference ( 100 level) for octane ratings. c. 2 -tert-butylpentane d. The names given in parts a and \(\mathrm{c}\) are incorrect. Give the correct names for these hydrocarbons.

The codons (words) in DNA (that specify which amino acid should be at a particular point in a protein) are three bases long. How many such three- letter words can be made from the four bases adenine, cytosine, guanine, and thymine?

Polycarbonates are a class of thermoplastic polymers that are used in the plastic lenses of eyeglasses and in the shells of bicycle helmets. A polycarbonate is made from the reaction of bisphenol A (BPA) with phosgene \(\left(\mathrm{COCl}_{2}\right)\) : polycarbonate \(+2 n \mathrm{HCl}\) Phenol \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\right)\) is used to terminate the polymer (stop its growth). a. Draw the structure of the polycarbonate chain formed from the above reaction. b. Is this reaction a condensation or an addition polymerization?

A chemical "breathalyzer" test works because ethanol in the breath is oxidized by the dichromate ion (orange) to form acetic acid and chromium(III) ion (green). The balanced reaction is \(3 \mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}(a q)+2 \mathrm{Cr}_{2} \mathrm{O}_{7}{ }^{2-}(a q)+2 \mathrm{H}^{+}(a q) \longrightarrow\) \(3 \mathrm{HC}_{2} \mathrm{H}_{3} \mathrm{O}_{2}(a q)+4 \mathrm{Cr}^{3+}(a q)+11 \mathrm{H}_{2} \mathrm{O}(l)\) You analyze a breathalyzer test in which \(4.2 \mathrm{mg} \mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}\) was reduced. Assuming the volume of the breath was \(0.500 \mathrm{~L}\) at \(30 .{ }^{\circ} \mathrm{C}\) and \(750 . \mathrm{mm} \mathrm{Hg}\), what was the mole percent alcohol of the breath?
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

The Earths Atmosphere

Read Explanation

Kinetics

Read Explanation

Chemical Analysis

Read Explanation

Physical Chemistry

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