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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1:53 minutes

Problem 117

Textbook Question

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

Verified step by step guidance

Step 1: Identify the type of reaction taking place. The given reactants include a brominated cycloalkane and methanol (CH3OH). This suggests a nucleophilic substitution reaction, likely an SN1 mechanism due to the tertiary carbon attached to the bromine atom.

Step 2: Analyze the structure of the starting material. The bromine atom is attached to a tertiary carbon, which is highly favorable for the formation of a stable carbocation intermediate during the SN1 reaction.

Step 3: Predict the first step of the reaction. The bromine atom will leave, forming a carbocation intermediate. This step is the rate-determining step in the SN1 mechanism.

Step 4: Consider the role of methanol (CH3OH). Methanol acts as a nucleophile and will attack the carbocation intermediate, forming a new bond between the oxygen atom of methanol and the carbon atom of the carbocation.

Step 5: Account for the final product. After the nucleophilic attack, a proton transfer will occur, resulting in the formation of an ether product. The final product will be a methoxy-substituted cycloalkane structure.

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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 bromide) by a nucleophile (such as methanol). These reactions can proceed via two main mechanisms: SN1, which is unimolecular and involves the formation of a carbocation intermediate, and SN2, which is bimolecular and involves a direct attack by the nucleophile. Understanding these mechanisms is crucial for predicting the products of the reaction.

Carbocation Stability

Carbocation stability is a key factor in determining the pathway of nucleophilic substitution reactions. Carbocations are positively charged species that can be stabilized by adjacent alkyl groups through hyperconjugation and inductive effects. The more stable the carbocation, the more likely the reaction will proceed via the SN1 mechanism, which is important for predicting the products formed in the given reaction.

E1 and E2 Elimination Reactions

E1 and E2 reactions are elimination processes that can occur alongside nucleophilic substitutions. E1 reactions involve the formation of a carbocation followed by the loss of a proton, while E2 reactions are concerted processes where the base abstracts a proton as the leaving group departs. Recognizing the conditions that favor elimination over substitution is essential for determining the final products in reactions involving alkyl halides and alcohols.

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Related Practice

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

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

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⁻

Textbook Question

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

c. CH₃S⁻

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