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

Substitution Comparison

Organic Chemistry

7. Substitution Reactions

Substitution Comparison

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Problem 106o(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.'
(o)

Verified step by step guidance

Identify the functional group in the given molecule. The molecule shown is a secondary alcohol, specifically a benzylic alcohol due to the presence of the benzene ring.

For condition (iii) with SOCl₂ and NEt₃: Recognize that SOCl₂ (thionyl chloride) is used to convert alcohols into alkyl chlorides. The reaction proceeds via an S_N2 mechanism, which inverts the configuration at the chiral center.

Predict the product for condition (iii): The hydroxyl group (OH) will be replaced by a chlorine atom (Cl), resulting in the formation of a benzylic chloride with inversion of stereochemistry.

For condition (iv) with 1. TsCl, Et₃N 2. NaCN: Understand that TsCl (tosyl chloride) in the presence of a base like Et₃N converts the alcohol into a tosylate, which is a good leaving group. This is followed by nucleophilic substitution with NaCN.

Predict the product for condition (iv): The hydroxyl group is first converted to a tosylate, and then the tosylate is displaced by the cyanide ion (CN⁻) from NaCN, resulting in the formation of a benzylic nitrile with retention of configuration.

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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 better leaving groups by forming tosylates. When combined with a base like Et₃N, it facilitates the substitution reaction where the tosylate can be further reacted with nucleophiles, such as NaCN. This process is essential for understanding how to predict the products of reactions involving alcohols and nucleophiles after tosylation.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. There are two main mechanisms: SN1, which involves a carbocation intermediate, and SN2, which is a concerted reaction. Recognizing the conditions and structure of the reactants helps in determining which mechanism will dominate and thus predicting the final products of the reactions described.

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Related Practice

Textbook Question

Starting with (R)-1-deuterio-1-propanol, how could you prepare

c. (R)-1-deuterio-1-methoxypropane?

Textbook Question

Even with an excess of cyanide, only one equivalent will react with the following dibromoalkane. To which carbon will the cyanide add? Predict the product and explain your choice.

Textbook Question

Suggest a mechanism for the following reactions.

(a) Substitution:

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃ ; (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ (vii) HCl; (viii) HBr; (ix) PCC; (x) H₂CrO₄ , H₂O (xi) HOCl, H₂O (xii) HIO₄ If no reaction occurs, write 'no reaction.'

(o)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃. If no reaction occurs, write 'no reaction.'

(k)

Textbook Question

Explain how 1-butanol can be converted into the following compounds:

Textbook Question

Explain how 1-butanol can be converted into the following compounds:

Textbook Question

cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they react with HO⁻.

b. Explain, by showing the mechanisms, why different substitution products are obtained.

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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.'(o)

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.'
(o)