Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

7. Substitution Reactions

SN2 Reaction

Organic Chemistry

7. Substitution Reactions

SN2 Reaction

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Problem 106f(iii,iv)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; If no reaction occurs, write 'no reaction.'
(f)

Verified step by step guidance

Identify the functional group in the given molecule. The structure shows a tertiary alcohol group attached to a benzene ring.

Consider the reaction conditions (iii) SOCl₂, NEt₃. This is a common method for converting alcohols to alkyl chlorides via the formation of a chlorosulfite intermediate.

In the presence of SOCl₂ and NEt₃, the hydroxyl group (OH) of the tertiary alcohol will be replaced by a chlorine atom, resulting in the formation of a tertiary alkyl chloride.

Now consider the reaction conditions (iv) 1. TsCl, Et₃N 2. NaCN. The first step involves converting the alcohol to a tosylate, which is a good leaving group, using TsCl and Et₃N.

In the second step, the tosylate reacts with NaCN, leading to a nucleophilic substitution where the tosylate group is replaced by a cyano group (CN), forming a nitrile.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Thionyl Chloride (SOCl₂) Reactivity

Thionyl chloride is a reagent commonly used for converting alcohols into alkyl chlorides. It reacts with alcohols to form the corresponding alkyl chloride and byproducts of sulfur dioxide and hydrochloric acid. Understanding this reaction mechanism is crucial for predicting the products when alcohols are treated with SOCl₂ in the presence of a base like NEt₃, which helps to neutralize the generated HCl.

TsCl and Base Reaction

TsCl, or tosyl chloride, is used to convert alcohols into tosylates, which are better leaving groups for subsequent nucleophilic substitutions. When combined with a base like Et₃N, the tosylate can then react with nucleophiles such as NaCN in a second step. This two-step process is essential for understanding how to predict the final products of the reaction sequence involving TsCl and NaCN.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution reactions, such as SN1 and SN2, are fundamental in organic chemistry for understanding how nucleophiles attack electrophiles. The choice of mechanism depends on factors like substrate structure and the nature of the nucleophile. Recognizing whether a reaction will proceed via SN1 or SN2 is vital for predicting the outcome of reactions involving alkyl halides and nucleophiles like NaCN.

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Related Practice

Textbook Question

Cardura, a drug used to treat hypertension, is synthesized as shown here.

b. Show the mechanism for conversion of A to B. Which is formed more rapidly, A or B?

Textbook Question

Propose a mechanism for the following reaction that explains why the configuration of the asymmetric center in the reactant is retained in the product:

Textbook Question

The S_N2 reaction is the concerted, backside displacement of a good leaving group by a nucleophile. Why do nucleophiles attack from the back in S_N2 reactions?

Textbook Question

For each pair, choose the haloalkane that would react most quickly in an S_N2 reaction.

(a)

Textbook Question

Practice your electron-pushing skills by drawing a mechanism for the following S_N2 reactions.

(c)

Textbook Question

For each pair, choose the nucleophile that would react most quickly in an S_N2 reaction (assume H₂O is the solvent).

(c)

Textbook Question

For each pair, choose the haloalkane that would react most quickly in an S_N2 reaction.

(c)

Textbook Question

In which solvent—ethanol or diethyl ether—would the equilibrium for the following S_N2 reaction lie farther to the right?

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Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; If no reaction occurs, write 'no reaction.'(f)

Key Concepts

Thionyl Chloride (SOCl₂) Reactivity

TsCl and Base Reaction

Nucleophilic Substitution Mechanisms

Watch next

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; If no reaction occurs, write 'no reaction.'
(f)