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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2:42 minutes

Problem 34f

Textbook Question

Predict the product(s) of the following reactions.
(f)

Verified step by step guidance

Step 1: Analyze the given reactant structure. The molecule contains a triazole ring, a benzyl chloride group, and a phenyl group. The reaction involves water (H₂O), which suggests hydrolysis or substitution might occur.

Step 2: Identify the reactive site. The benzyl chloride group (C-Cl bond) is a good candidate for nucleophilic substitution because the benzyl position is activated for such reactions.

Step 3: Consider the mechanism. In the presence of water, the reaction likely proceeds via an SN1 mechanism due to the stability of the benzyl carbocation formed after the departure of the chloride ion.

Step 4: Predict the product. The nucleophile (H₂O) will attack the benzyl carbocation, leading to the formation of a benzyl alcohol group (-CH₂OH) in place of the chloride.

Step 5: Finalize the structure of the product. The triazole ring and phenyl group remain unchanged, while the benzyl chloride group is converted to a benzyl alcohol group. The product is 1-(1H-1,2,4-triazol-1-yl)-2-phenylethanol.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophilic carbon atom, replacing a leaving group. In this case, the chlorine atom acts as the leaving group, and water can act as a nucleophile, leading to the formation of a new bond. Understanding this mechanism is crucial for predicting the products of the reaction.

Electrophilicity of Halogens

Halogens, such as chlorine, are highly electronegative and can stabilize a positive charge, making them good leaving groups in substitution reactions. The presence of chlorine in the compound indicates that it can be replaced by a nucleophile like water. Recognizing the role of halogens in organic reactions helps in predicting the outcome of the reaction.

Reaction Conditions and Solvent Effects

The solvent used in a reaction can significantly influence the mechanism and rate of the reaction. In this case, water serves as a polar protic solvent, which can stabilize charged intermediates and facilitate the nucleophilic attack. Understanding how solvents affect reaction pathways is essential for predicting the products and yields of organic reactions.

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Suggest a reagent to carry out each of the following conversions to an alcohol.

(a)

Textbook Question

When (R)-(1-bromoethyl)benzene is treated with sodium cyanide, a single enantiomer is produced. However, upon treatment of the same molecule with water, a mixture of two enantiomers is obtained.

(a) Explain these results.

(b) Why is only partial racemization sometimes observed?

Textbook Question

Order the following molecules on the basis of their nucleophilic strength using the pKₐ values of their conjugate acids.

Textbook Question

Suggest a reagent to carry out each of the following conversions to an alcohol.

(c)

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Predict the product(s) of the following reactions.

(g)

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When trans-4-bromocyclohexanol is treated with base, an intramolecular substitution reaction occurs to give a cyclic ether. This product does not form when cis-4-bromocyclohexanol is reacted under the same conditions. Explain these observations.

Textbook Question

Which of the following reactions take place more rapidly when the concentration of the nucleophile is increased?

Textbook Question

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

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

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