ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
2nd Edition
ISBN: 9780393664034
Author: KARTY
Publisher: NORTON
bartleby

Concept explainers

bartleby

Videos

Question
Book Icon
Chapter 13, Problem 13.9P
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.

The alkylation at alpha carbon atoms in ketones is regioselective, and we can control the regioselectivity by using appropriate reagents and the sequence in which the reagents are used. The choice of base dictates which alpha carbon undergoes reaction. A very strong base such as LDA leads to alkylation at the less substituted alpha carbon atom whereas a moderately strong base such as tert-butoxide anion leads to alkylation at the more substituted alpha carbon atom. The alkylation occurs using an alkyl halide as an alkylating group.

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.

The alkylation at the alpha carbon atoms in ketones is regioselective, and we can control the regioselectivity using appropriate reagents, and the sequence in which the reagents are used. The choice of base dictates which alpha carbon undergoes a reaction. A very strong base such as LDA leads to alkylation at the less substituted alpha carbon atom. whereas a moderately strong base such as tert-butoxide anion leads to alkylation at the more substituted alpha carbon atom. The alkylation occurs using an alkyl halide as an alkylating group.

Blurred answer
Students have asked these similar questions
(SYN) In the reaction shown here, the aromatic ring has just one chemically distinct, aromatic H, so a single electrophilic aromatic substitution will lead to just a single product. With this in mind, supply the missing reagentsneeded to carry out the transformation.
Please predict the product of the following reaction, and draw the complete, detailed mechanism.
Textbook problem: Suggest short series of reactions that would be expected to transform the material on the right into the desired product shown on left.
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