7. You are planning a synthesis to transform the following alcohol into a nitrile. However, ahydroxyl group is not a good leaving group in SN2 reactions. How would you solve the problem?OHCNNa CNTHFOCH3CH3Better leaving group

Explanation Nucleophilic substitution reaction If one nucleophile replaced by another nucleophile…

Answered: 7. You are planning a synthesis to…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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7. You are planning a synthesis to transform the following alcohol into a nitrile. However, a
hydroxyl group is not a good leaving group in SN2 reactions. How would you solve the problem?
OH
CN
Na CN
THF
OCH3
CH3
Better leaving group

Expert Solution

Step 1

Explanation

Nucleophilic substitution reaction

If one nucleophile replaced by another nucleophile called Nucleophilic substitution reaction.
Reactivity of nucleophile is called nucleophilicity it is kinetic term but basicity is thermodynamic term.
In periods nucleophilicity direct prepositional to basicity
In group nucleophilicity α 1/basicity
SN² reaction

Substrate:
- Best in primary alkyl halide
- Works for secondary alkyl halide, fails if tertiary.
Reaction is:
- Concerted reaction means no intermediate is present, transition state is present and
- it is single step reaction and all bonds are form and break at same time
- This reaction stereospecific reaction that means Walden inversion taking place in this reaction (umbrella).
- Bimolecular reaction: rate depends on concentration of both nucleophile and substrate.
Nucleophile:
- Best if more reactive that means more ionic or more basic.
Leaving group:
- TsO is very good leaving group.
Following orders

TsO › I^- › Br^- ›Cl^- › F^- (very poor)
- Basicity order is CH3^-› NH2^- › OH^- ›F^-
- Leaving Groups on double-bonded carbons are never replaced by SN2 reaction.
Solvent
- Polar Aprotic (i.e. no OH) is best
Example; dimethylformamide, dimethylsulfoxide, acetonitrile

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