Determine the mechanism for cleavage reaction of the p-Dimethoxytrityl (DMT) ether. Concept introduction: The cleavage reaction of p-Dimethoxytrityl (DMT) takes place by the S N 1 mechanism. The S N 1 reaction is nucleophilic substitution reaction in which nucleophile is replaced by a leaving group. S N 1 indicates unimolecular, substitution and nucleophilic reaction. S N 1 reaction takes place in following two steps: Leaving group leaves and leaves behind carbocation intermediate. Nucleophilic attack on the carbocation to form final product. The stability of carbocation i.e. 3°>2°>1°, determines the rate of the reaction. Given information: The information given in the question is that the DMT ether is easily cleaved by the treatment with mild acid.

Question

#1. Retro-Electrochemical Reaction: A ring has been made, but the light is causing the molecule to un- cyclize. Undo the ring into all possible molecules. (2pts, no partial credit) hv

Answer 1

Question

Chapter 28.7, Problem 11P

Interpretation Introduction

Interpretation:

Determine the mechanism for cleavage reaction of the p-Dimethoxytrityl (DMT) ether.

Concept introduction:

The cleavage reaction of p-Dimethoxytrityl (DMT) takes place by the S_N1 mechanism. The S_N1 reaction is nucleophilic substitution reaction in which nucleophile is replaced by a leaving group. S_N1 indicates unimolecular, substitution and nucleophilic reaction.

S_N1 reaction takes place in following two steps:

Leaving group leaves and leaves behind carbocation intermediate.

Nucleophilic attack on the carbocation to form final product.

The stability of carbocation i.e. 3°>2°>1°, determines the rate of the reaction.

Given information:

The information given in the question is that the DMT ether is easily cleaved by the treatment with mild acid.

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#1. Retro-Electrochemical Reaction: A ring has been made, but the light is causing the molecule to un- cyclize. Undo the ring into all possible molecules. (2pts, no partial credit) hv

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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."