Nucleophilic Substitution: The Three Rules

Problem: Determine the major product for the following reaction.

4m

Problem: Determine the major product for the following reaction. 

3m

Problem: Determine the major product for the following reaction. 

2m

Problem: Determine the major product for the following reaction. 

2m

Nucleophilic Substitution: The Three Rules Additional Practice Problems

Give step by step mechanism for the following transformation:

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Complete the following reaction supplying the missing product and showing correct regio- and stereochemistry where applicable. If a racemic or diastereomeric mixture forms show all stereoisomers; if no reaction takes place, write N.R.

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Arrange the following compounds so that reactivity towards aqueous potassium hydroxide increases from left to right.

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Predict the products and indicate the relative stereochemistry for the following transformations. When necessary indicate the major product.

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Draw the organic product(s) of the following reaction. Indicate stereochemistry where appropriate. A reasonable answer may be “ No Reaction.”

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Draw the organic product(s) for the following reaction. Indicate stereochemistry where appropriate. Assume an aqueous workup, when necessary. A reasonable answer may be “ No Reaction.”

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Consider the formation of an amide from an ester. 

An estimate of the overall enthalpy of this transformation using the bond dissociation energies given below is 

1) 13 kcal/mol     2) – 4 kcal/mol     3) – 17 kcal/mol 4) 7 kcal/mol    5) –11 kcal/mol

Bond dissociation energies (kcal/mol) 

C–H                                      99

C–O                                      79

C–C                                      85

C–N                                      66

R2N–H                                 92

C=O                                    175

C=N                                    145

RO–H                                 109

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Which reaction would not proceed in good yield as written?

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Draw the major product(s) for the following reaction. Assume the nucleophile is in excess. If there will be no reaction, write NR.

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Determine the necessary reagent and provide the mechanism for the reaction below.

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Rank in order of decreasing reactivity in toward nucleophilic addition-elimination.

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Show the product(s) for the acid catalyzed reaction between formic acid and 1-pentanol. 

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Provide the product for the following reaction. 

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Choose the reaction coordinate that best describes the following reaction.

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Which reaction is the  least favorable (lowest Keq)?

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Predict the product(s) formed in the following reaction.

 

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Predict the product for the following reaction

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Predict the major product for the following reaction, paying attention to the regio- and stereochemistry where appropriate. 

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Predict the major product for the following reaction, paying attention to the regio- and stereochemistry where appropriate. 

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What is the final principal organic product from the following transformation?

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What is the result of treating benzoyl chloride with aniline followed by LiAlH 4 then water?

a) PhNHCH2Ph (Ph = phenyl)

b) Diphenylamine

c) Dibenzylamine

d) N-Phenylbenzamide

e) None of the above

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