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

SN1 Reaction

Organic Chemistry

7. Substitution Reactions

SN1 Reaction

Previous problemNext problem

5:51 minutes

Problem 45c,d

Textbook Question

Predict the products of the following S_N2 reactions.
(c)

(d)

Verified step by step guidance

Step 1: Identify the type of reaction. Both reactions are SN2 reactions, which involve a single-step mechanism where the nucleophile attacks the electrophilic carbon and displaces the leaving group simultaneously.

Step 2: Analyze the reactants in reaction (c). The nucleophile is the phenylthiolate ion (C6H5S⁻), and the electrophile is ethyl bromide (CH3CH2Br). The bromine atom is the leaving group.

Step 3: Predict the product for reaction (c). The phenylthiolate ion will attack the electrophilic carbon in ethyl bromide, forming a new bond between the sulfur atom and the ethyl group. Bromine will be displaced as Br⁻.

Step 4: Analyze the reactants in reaction (d). The nucleophile is the acetylide ion (Na⁺:C≡CH), and the electrophile is a long-chain alkyl chloride (CH3(CH2)8CH2Cl). The chlorine atom is the leaving group.

Step 5: Predict the product for reaction (d). The acetylide ion will attack the electrophilic carbon in the alkyl chloride, forming a new bond between the terminal carbon of the acetylide and the alkyl chain. Chlorine will be displaced as Cl⁻.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

SN2 Mechanism

The SN2 mechanism is a type of nucleophilic substitution reaction where a nucleophile attacks an electrophile, resulting in the simultaneous displacement of a leaving group. This reaction occurs in a single concerted step, leading to the inversion of configuration at the carbon center. It is characterized by a bimolecular rate law, meaning the rate depends on the concentration of both the nucleophile and the substrate.

Nucleophiles

Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. In SN2 reactions, nucleophiles are typically negatively charged or neutral molecules with lone pairs of electrons. In the given reaction, sodium thiolate (S-) acts as the nucleophile, attacking the electrophilic carbon in bromoethane (CH3CH2Br) to form a new bond.

Leaving Groups

Leaving groups are atoms or groups that can depart from the substrate during a chemical reaction, taking with them the electrons from the bond they formed with the substrate. A good leaving group is typically stable after departure and can be a halide ion (like Br- in this case). The ability of a leaving group to leave easily is crucial for the success of SN2 reactions, as it influences the reaction rate and product formation.

Watch next

Master Drawing the SN1 Mechanism with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:

(d) a 3° alkyl bromide

Textbook Question

Give the substitution products expected from solvolysis of each compound by heating in ethanol.

(c)

(d)

Textbook Question

Propose a mechanism for the reaction of benzyl bromide with ethanol to give benzyl ethyl ether.

Textbook Question

Propose a mechanism involving a hydride shift or an alkyl shift for each solvolysis reaction. Explain how each rearrangement forms a more stable intermediate.

Hint: Most rearrangements convert 2° (or incipient 1°) carbocations to 3° or resonance-stabilized carbocations.

(d)

Textbook Question

Choose the member of each pair that will react faster by the SN1 mechanism.

e. 2-iodo-2-methylbutane or tert-butyl chloride

f. 2-bromo-2-methylbutane or ethyl iodide

Textbook Question

When tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether.

b. What happens to the rate if the concentration of tert-butyl bromide is tripled and the concentration of ethanol is doubled?

c. What happens to the rate if the temperature is raised?

Textbook Question

tert-Butyl chloride undergoes solvolysis in both acetic acid and formic acid. Solvolysis occurs 5000 times faster in one of these two solvents than in the other. In which solvent is solvolysis faster? Explain your answer. (Hint: Formic acid is more polar than acetic acid.)

Textbook Question

Rank the following alkyl halides from most reactive to least reactive in an S_N1 reaction:

2-bromo-2-methylpentane, 2-chloro-2-methylpentane, 3-chloropentane, and 2-iodo-2-methylpentane.

Show more practices