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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3:19 minutes

Problem 126

Textbook Question

Predict the product for the following reaction and write a mechanism to explain how it is formed.

Verified step by step guidance

Step 1: Analyze the reactants and reaction conditions. The reactant is an allylic bromide (a bromine atom attached to a carbon adjacent to a double bond). The solvent is methanol (CH₃OH), which can act as a nucleophile.

Step 2: Recognize the reaction type. This is likely an SN1 reaction due to the allylic bromide's ability to form a stable carbocation intermediate. Allylic carbocations are stabilized by resonance, making the SN1 pathway favorable.

Step 3: Write the first step of the mechanism. The bromine atom leaves, forming an allylic carbocation. This carbocation is stabilized by resonance, meaning the positive charge is delocalized over the π system of the double bonds.

Step 4: Identify the nucleophile's role. Methanol (CH₃OH) acts as the nucleophile and attacks the carbocation at the positively charged carbon. This results in the formation of a new bond between the carbon and the oxygen atom of methanol.

Step 5: Complete the mechanism. After the nucleophilic attack, a proton from the methanol group is removed by a base (possibly another methanol molecule), resulting in the final product: an ether with the methoxy group (-OCH₃) attached to the allylic position.

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Key Concepts

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

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group (like Br) by a nucleophile (like CH3OH). In these reactions, the nucleophile donates a pair of electrons to form a new bond, while the leaving group departs with its electrons. The two main types are SN1, which involves a two-step mechanism with a carbocation intermediate, and SN2, which is a one-step mechanism where the nucleophile attacks the substrate simultaneously as the leaving group departs.

Carbocation Stability

Carbocation stability is crucial in predicting the outcome of nucleophilic substitution reactions, particularly in SN1 mechanisms. Carbocations are positively charged species that can be stabilized by adjacent alkyl groups through hyperconjugation and inductive effects. The more substituted the carbocation (tertiary > secondary > primary), the more stable it is, influencing the likelihood of the reaction pathway taken.

Mechanism of SN1 Reactions

The mechanism of SN1 reactions consists of two main steps: formation of a carbocation intermediate and nucleophilic attack. Initially, the leaving group departs, forming a carbocation. This is followed by the nucleophile attacking the carbocation to form the final product. The rate of the reaction depends only on the concentration of the substrate, making it a unimolecular process, which is characteristic of SN1 reactions.

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Related Practice

Textbook Question

a. Draw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol.

b. Are all the products optically active?

Textbook Question

What are the products of the following reactions?

Textbook Question

What are the products of the following reactions?

Textbook Question

For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.

d. trans-1-chloro-3-methylcyclohexane + high concentration of CH₃O⁻

Textbook Question

Draw the structures of the products obtained from the following reaction:

Textbook Question

Draw the products of each of the following S_N2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

a. (3S,4S)-3-bromo-4-methylhexane + CH₃O⁻

Textbook Question

For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.

c. trans-1-chloro-2-methylcyclohexane + high concentration of CH₃O⁻

Textbook Question

What product is formed when 1-bromopropane reacts with each of the following nucleophiles?

d. HS⁻

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