EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393543971
Author: KARTY
Publisher: VST
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Chapter D, Problem D.6P
Interpretation Introduction

Interpretation:

The approach of the Br- on the (CH3)3C+ carbocation from within the plane of the central C atom in the coordination step is to be discussed.

Concept introduction:

In the coordination step, a substrate undergoes substitution, in which the nucleophile is attached to the electrophile. The conjugate bases of strong acids act as nucleophiles. The negative charged nucleophile is attracted to an atom bearing a positive charge on the electrophile. However, for the bond formation between a nucleophile and an electrophile, only a single covalent bond is formed. Nucleophile is the electron rich species, and it will contribute the HOMO interaction, and electron poor C atom will contribute the LUMO interaction. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) must have axial overlap or parallel overlap. The axial overlap between HOMO and LUMO has substantial net overlap, so this reaction is allowed. If the HOMO and LUMO do not have a substantial overlap, this overlap is forbidden.

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I have a question about this problem involving mechanisms and drawing curved arrows for acids and bases. I know we need to identify the nucleophile and electrophile, but are there different types of reactions? For instance, what about Grignard reagents and other types that I might not be familiar with? Can you help me with this? I want to identify the names of the mechanisms for problems 1-14, such as Gilman reagents and others. Are they all the same? Also, could you rewrite it so I can better understand? The handwriting is pretty cluttered. Additionally, I need to label the nucleophile and electrophile, but my main concern is whether those reactions differ, like the "Brønsted-Lowry acid-base mechanism, Lewis acid-base mechanism, acid-catalyzed mechanisms, acid-catalyzed reactions, base-catalyzed reactions, nucleophilic substitution mechanisms (SN1 and SN2), elimination reactions (E1 and E2), organometallic mechanisms, and so forth."
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