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Below is an analysis for a nucleophilic substitution reaction. Read the analysis

ID: 942157 • Letter: B

Question


Below is an analysis for a nucleophilic substitution reaction. Read the analysis then critique the presented solution [Determine if the solution is correct or not. Write a paragraph on how you would convey the same information (include corrections or suggestions to improve the analysis presented). the reaction shown would proceed via a S,1 reaction mechanism. More specifically this is a solvolysis reaction in which the solvent acts as the nucleophile for the reaction. the first step in this reaction would be the solvation of the reactant molecule followed by the departure of the leaving group, in this case, bromide This will generate a carboanion which flattens out into a planar structure. the empty p orbital can then be attacked on either side by methoxide. This leads to a racemic mixture of enantiomers of 3-methoxy-3methylhexane. the polar aprotic solvent assists in solvating the bromide leaving group. Since methanol is a very weak base, there is little chance of ar elimination reaction occurring One thing that isn't mentioned in the reaction Is temperature At higher temperatures, the reaction product will be the predominate product of the reaction and the El reaction will become even less likely.

Explanation / Answer

This is definitely a SN1 reaction goes through the formation of carbo cation intermediate. Firstly Bromide ion gets departed from the substrate giving a carbo cation which is flat planar intermediate with empty p orbital that can be attacked by methanol through oxygen from either of the faces resulting a racemic mixture of the products 3-methoxy 3-methyl hexane. At higher temperature elimination product is predominant over Sn1 substitution product.

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