Reactivity in Chemistry

Aliphatic Nucleophilic Substitution

NS19. Extra Problems with Nucleophilic Substitution & Elimination

Problem NS19.1.

Fill in the missing items in the following synthesis.  Includes:  aliphatic nucleophilic substitution, carboxylic substitution, enolates, addition to carbonyl (anionic nucleophiles).

Problem NS19.2.

Fill in the missing items in the following synthesis.  Includes:  addition to carbonyls (anionic nucleophiles, neutral nucleophiles, aliphatic nucleophilic substitution, Mitsunobu reaction).

Problem NS19.3.

Fill in the missing items in the following synthesis.  Includes:  aliphatic nucleophilic substitution,sulfonate substitution, Mitsunobu reaction, silyl ether cleavage, nucleophilic substitution of epoxides, elimination / dehydration.

Problem NS19.4.

Fill in the missing items in the following synthesis.  Includes:   addition to carbonyls (ylides),  nucleophilic substitution of epoxides, carboxylic substitution.

Problem NS19.5.

Fill in the missing items in the following synthesis.  Includes: aliphatic nucleophilic substitution, carboxylic substitution, sulfonate substitution, addition to nitriles, addition to carbonyls (ylides).

Problem NS19.6.

Fill in the missing items in the following synthesis.  Includes:  aliphatic nucleophilic substitution, carbonyl addition (anionic nucleophiles, acetals, ylides), carboxylic substitution, silyl ethers.

Problem NS19.7.

Fill in the missing items in the following synthesis.  Includes:  aliphatic nucleophilic substitution, sulfonate substitution, elimination.

 

Problem NS19.8.

Predict products of the following reactions.

 

Problem NS19.9.

Predict products of the following reactions.

 

Problem NS19.10.

Predict products of the following reactions.

 

Problem NS19.11.

Predict products of the following reactions.

 

Problem NS19.12.

Predict products of the following reactions.

 

Problem NS19.13.

Predict products of the following reactions.

 

With contributions from Kate Graham and Nicholas Jones.

This site is written and maintained by Chris P. Schaller, Ph.D., College of Saint Benedict / Saint John's University (with contributions from other authors as noted).  It is freely available for educational use.

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Structure & Reactivity in Organic, Biological and Inorganic Chemistry by Chris Schaller is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License

Send corrections to cschaller@csbsju.edu

This material is based upon work supported by the National Science Foundation under Grant No. 1043566.

Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation.

 

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