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

8. Elimination Reactions

Cumulative Substitution/Elimination

Organic Chemistry

8. Elimination Reactions

Cumulative Substitution/Elimination

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Problem 106c(i,iii)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (iii) SOCl₂, NEt₃. If no reaction occurs, write 'no reaction.'
(c)

Verified step by step guidance

Identify the functional groups in the given molecule. The structure shows a cyclohexane ring with two hydroxyl groups (OH) attached, indicating it is a diol.

Consider the reaction conditions: (i) SOCl₂ and (iii) SOCl₂, NEt₃. Thionyl chloride (SOCl₂) is commonly used to convert alcohols into alkyl chlorides.

For condition (i) with SOCl₂ alone, each hydroxyl group can be converted into a chloride group. The reaction typically proceeds via an S_N2 mechanism, where the hydroxyl group is replaced by a chlorine atom.

For condition (iii) with SOCl₂ and NEt₃ (triethylamine), the presence of a base like NEt₃ helps to neutralize the HCl byproduct and can facilitate the reaction, especially for secondary and tertiary alcohols.

Predict the product: Each hydroxyl group in the diol will be replaced by a chlorine atom, resulting in a dichloride compound. The cyclohexane ring remains unchanged, and the two chlorine atoms will be attached to the same carbon atoms where the hydroxyl groups were originally located.

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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 versatile reagent in organic chemistry, primarily used for converting alcohols into alkyl chlorides. The reaction typically involves the nucleophilic substitution mechanism, where the hydroxyl group is replaced by a chloride ion. Understanding the reactivity of SOCl₂ helps predict the products formed when it reacts with various functional groups.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution is a fundamental reaction type in organic chemistry where a nucleophile replaces a leaving group in a molecule. There are two main mechanisms: SN1, which involves a two-step process with a carbocation intermediate, and SN2, which is a one-step process involving a direct attack by the nucleophile. Recognizing which mechanism is favored in a given reaction is crucial for predicting the outcome.

Base Effects in Reactions

The presence of a base, such as triethylamine (NEt₃), can influence the course of a reaction significantly. In the context of reactions with SOCl₂, NEt₃ can act to deprotonate any acidic protons, facilitating the formation of a better leaving group or stabilizing intermediates. Understanding how bases interact with reactants is essential for predicting whether a reaction will proceed and what products will form.

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Related Practice

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.'

(c)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'

(o)

Textbook Question

(k)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vi) H₂SO₄. If no reaction occurs, write 'no reaction.'

(c)

Textbook Question

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

(c)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vii) HCl; (viii) HBr; If no reaction occurs, write 'no reaction.'

(c)

Textbook Question

(f)

Textbook Question

Predict the product(s) of the following substitution or elimination reactions, paying close attention to the stereochemical outcome of the reactions.

(a)

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