Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
bartleby

Concept explainers

bartleby

Videos

Question
Book Icon
Chapter 13, Problem 13.10P
Interpretation Introduction

(a)

Interpretation:

How the given transform would appear in a synthesis is to be shown.

Concept introduction:

A synthetic trap is a synthesis which prevents the reaction from occurring in the forward direction as planned. This occurs mainly because the reactant molecule contains multiple functional groups which interfere in the desired mechanism. However, even when there is only one functional group, a synthetic trap can still arise if a reaction takes place at two or more sites within that functional group. In such cases, regiochemistry is an issue. Regiochemistry is the specific region in the given molecule at which the reaction takes place selectively. We can choose a synthesis according to the regioselectivities of the functional group transformation reactions.

In epoxide ring opening reactions, the regiochemistry can be controlled by using acidic or basic/neutral medium. The nucleophile tends to attack the most substituted carbon atom under acidic conditions whereas a nucleophile tends to attack the least substituted carbon atom under neutral or basic conditions.

Interpretation Introduction

(b)

Interpretation:

How the given transform would appear in a synthesis is to be shown.

Concept introduction:

A synthetic trap is a synthesis which prevents the reaction from occurring in the forward direction as planned. This occurs mainly because the reactant molecule contains multiple functional groups which interfere in the desired mechanism. However, even when there is only one functional group, a synthetic trap can still arise if a reaction takes place at two or more sites within that functional group. In such cases, regiochemistry is an issue. Regiochemistry is the specific region in the given molecule at which the reaction takes place selectively. We can choose a synthesis according to the regioselectivities of the functional group transformation reactions.

In epoxide ring opening reactions, the regiochemistry can be controlled using acidic or basic/neutral medium. The nucleophile tends to attack the most substituted carbon atom under acidic conditions whereas a nucleophile tends to attack the least substituted carbon atom under neutral or basic conditions.

Blurred answer
Students have asked these similar questions
03 Question (1 point) For the reaction below, draw both of the major organic products. Be sure to consider stereochemistry. > 1. CH₂CH₂MgBr 2. H₂O 3rd attempt Draw all four bonds at chiral centers. Draw all stereoisomers formed. Draw the structures here. e 130 AN H See Periodic Table See Hint P C Br
You may wish to address the following issues in your response if they are pertinent to the reaction(s) you propose to employ:1) Chemoselectivity (why this functional group and not another?) 2) Regioselectivity (why here and not there?) 3) Stereoselectivity (why this stereoisomer?) 4) Changes in oxidation state.   Please make it in detail and draw it out too in what step what happens. Thank you for helping me!
1) Chemoselectivity (why this functional group and not another?)   2) Regioselectivity (why here and not there?)   3) Stereoselectivity (why this stereoisomer?)   4) Changes in oxidation state.  Everything in detail and draw out and write it.
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License