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

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

Organic Chemistry

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

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1:47 minutes

Problem 8

Textbook Question

Predict the products of the following reactions.
(c) benzyl bromide + sodium cyanide

Verified step by step guidance

Step 1: Identify the type of reaction. Benzyl bromide reacts with sodium cyanide (NaCN) in a nucleophilic substitution reaction. The bromine atom is a good leaving group, and the cyanide ion (CN⁻) acts as a nucleophile.

Step 2: Analyze the structure of benzyl bromide. Benzyl bromide consists of a benzene ring attached to a CH₂ group, which is further bonded to a bromine atom. The CH₂-Br bond is susceptible to nucleophilic attack.

Step 3: Determine the mechanism. This reaction typically proceeds via an SN2 mechanism because the benzyl position is sterically unhindered, allowing the cyanide ion to directly attack the carbon bonded to bromine.

Step 4: Predict the product. The cyanide ion replaces the bromine atom, forming benzyl cyanide (C₆H₅CH₂CN). The benzene ring remains intact, and the CH₂ group is now bonded to the cyanide group.

Step 5: Write the chemical equation. The reaction can be represented as:

{C 6 H 5}_{CH 2} (Br) + {Na CN}_{(aq) \to {C 6 H 5}_{CH 2} (CN) + {Na}_{Br}}

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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 electrophile, resulting in the replacement of a leaving group. In this case, sodium cyanide (NaCN) acts as the nucleophile, attacking the carbon atom bonded to the bromine in benzyl bromide, leading to the formation of a new bond and the release of bromide ion.

Benzyl Bromide Reactivity

Benzyl bromide is a primary alkyl halide, which makes it highly reactive towards nucleophiles due to the accessibility of the carbon atom bonded to the bromine. The presence of the benzyl group stabilizes the transition state during the nucleophilic substitution, facilitating the reaction with sodium cyanide to form benzyl cyanide.

Formation of Nitriles

The reaction of benzyl bromide with sodium cyanide results in the formation of a nitrile, specifically benzyl cyanide. Nitriles are characterized by the presence of a cyano group (-C≡N), which is formed when the nucleophile (cyanide ion) replaces the leaving group (bromide ion). This transformation is significant in organic synthesis, as nitriles can be further converted into various functional groups.

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