The reason has to be explained for the given compound does not undergo a nucleophilic substitution reaction by either S N 1 or S N 2 mechanisms. Concept introduction: S N 1 reaction: The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product. Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it wonâ€™t undergo S N 1 substitution reaction. S N 2 reaction: Tosylated compound is reaction with sodium methoxide which undergoes again S N 2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below, Given information: The given compound is shown below,

Question

Imines are electrophiles in the related Mannich reaction. Draw two transition states, one leading to the syn diastereomer and one leading to the anti. Briefly explain which is favoured and why. Assume the imine doesn't change geometry. OM H3G CH3 Ph CH3

Answer 1

Question

Chapter 11.SE, Problem 32MP

Interpretation Introduction

Interpretation:

The reason has to be explained for the given compound does not undergo a nucleophilic substitution reaction by either S_N1 or S_N2 mechanisms.

Concept introduction:

S_N1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it wonâ€™t undergo S_N1 substitution reaction.

S_N2 reaction:

Tosylated compound is reaction with sodium methoxide which undergoes again S_N2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

Given information:

The given compound is shown below,

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Imines are electrophiles in the related Mannich reaction. Draw two transition states, one leading to the syn diastereomer and one leading to the anti. Briefly explain which is favoured and why. Assume the imine doesn't change geometry. OM H3G CH3 Ph CH3

The reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs due to a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain what this observation tells about the mechanism of the reaction.

Compounds X and Y are both C7H15Cl products formed in the radical chlorination of 2,4-dimethylpentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C7H₁4 alkene. Both X and Y undergo an SN2 reaction with sodium iodide in acetone solution to give C7H15l products; in this reaction Y reacts faster than X. What is the structure of X? • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. . Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. на