Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 17: Problem 375

Draw structures showing stereochemistry where necessary for the products you would expect from the following reactions.

Short Answer

Expert verified
In summary, the products for the given cases are: 1. Addition Reaction: 2-bromopropane (CH3CH(Br)CH3) 2. Substitution Reaction: (S)-2-cyanobutane (CH3CH(CN)CH2CH3) 3. Elimination Reaction: trans-2-butene (CH3CH=CHCH3)

Step by step solution

01

Identify the reactants

We will consider the addition of HBr to propene CH3CH=CH2 as an example. The reactants are propene and HBr.
02

Understand the mechanism

This is an electrophilic addition reaction: HBr dissocates into H+ and Br-, and propene forms a bond with H+, generating an intermediate carbocation.
03

Analyze the potential products

There will be two possible carbocations: a secondary carbocation CH3CH(Br)CH3 if the H+ reacts with the outer double bond carbon and a primary carbocation CH3(CH2)CH2+ if the H+ reacts with the inner carbon.
04

Determine the most stable carbocation

A secondary carbocation is more stable than a primary carbocation, so the major product will consist of the following structure: CH3CH(Br)CH3.
05

Draw the product and consider stereochemistry

In this case, stereochemistry doesn't matter since there is no chiral carbon. The product will be 2-bromopropane: CH3CH(Br)CH3. #Case 2: Substitution Reaction - SN2 reaction#
06

Identify the reactants

Let us consider the reaction of sodium cyanide, NaCN, with (R)-2-bromobutane (CH3CH(Br)CH2CH3) as an example.
07

Understand the mechanism

The mechanism of this reaction is SN2, where CN- attacks the chiral carbon from the backside and Br- leaves.
08

Determine the product with stereochemistry

The product will be (S)-2-cyanobutane since the stereochemistry will be inverted at the chiral center. The structure is: CH3CH(CN)CH2CH3. #Case 3: Elimination Reaction - E2 reaction#
09

Identify the reactants

Let's consider the reaction of (S)-2-bromobutane (CH3CH(Br)CH2CH3) with potassium tert-butoxide (KOtBu) as an example.
10

Understand the mechanism

This is an E2 reaction, a concerted process where the base abstracts the beta-hydrogen, and the halogen leaves, forming a double bond in the process.
11

Identify the beta-hydrogens and potential products

There are two possible beta-hydrogens, one on the CH2 between CH(Br)CH2CH3 and another on CH3CH(Br)CH2CH3.
12

Determine the more substituted and stable alkene

The more substituted alkene formed when KOtBu abstracts the beta-hydrogen from CH3CH(Br)CH2CH3 will be the major product.
13

Draw the major product and consider stereochemistry

The product is trans-2-butene where the double bond is formed between CH3 and CH2-CH3. No stereochemistry is needed as there is no chiral center.

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

Write equations for the reaction of ethylene oxide with methanol in the presence of a little \(\mathrm{H}_{2} \mathrm{SO}_{4} ;\) (b) methanol in the presence of a little \(\mathrm{CH}_{3} \mathrm{O}^{(-)} \mathrm{Na} \oplus ;\) (c) aniline.

Write a mechanism for the reaction of trans-2-butene with trifluoroperacetic acid which is consistent with the fact that the rate is first order in each participant and gives cis addition.

Outline a method of synthesizing \(\alpha\) -phenylethyl tert-buty1 ether from styrene and tert-butyl alcohol. Any inorganic reagents may be employed.

Specify a simple chemical test to distinguish the following pairs of compounds . Give the reagent to be used and the observation that you would make. (a) Diisopropyl ether and diallyl ether (b) Diethyl ether and methyl iodide (c) Dibutyl ether and \(\mathrm{n}\) -butyl alcohol

Name each of the following compounds: (a) \(\mathrm{CH}_{3}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\) (b) \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2}\right)_{2}-\mathrm{O}\) (c) \(\left(\mathrm{CH}_{3}\right){ }_{2} \mathrm{CH}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{3}\) (e) \(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{OH}\) (f) CC(Cl)CC1CO1
See all solutions

Recommended explanations on Chemistry Textbooks

Kinetics

Read Explanation

Making Measurements

Read Explanation

The Earths Atmosphere

Read Explanation

Chemistry Branches

Read Explanation

Organic Chemistry

Read Explanation

Ionic and Molecular Compounds

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