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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4:30 minutes

Problem 54b

Textbook Question

Write a balanced equation for each reaction, showing the major product you expect.
(b)

Verified step by step guidance

Step 1: Analyze the reactants. The given molecule is a bromocyclohexane derivative with a bromine atom attached to a carbon in the ring. The reagent is sodium tert-butoxide (NaOC(CH3)3), which is a strong base and sterically hindered.

Step 2: Consider the reaction mechanism. Sodium tert-butoxide typically promotes an elimination reaction (E2 mechanism) due to its strong basicity and steric hindrance. In an E2 reaction, the base abstracts a proton from a β-carbon (a carbon adjacent to the carbon bonded to the leaving group), and the leaving group (Br) departs simultaneously, forming a double bond.

Step 3: Identify the β-hydrogens. In the given molecule, the β-carbons are the carbons adjacent to the carbon bonded to bromine. The β-hydrogens are the hydrogens attached to these β-carbons. The stereochemistry of the molecule suggests that the elimination will occur in an anti-periplanar geometry, where the β-hydrogen and the leaving group (Br) are opposite to each other in the same plane.

Step 4: Predict the major product. The elimination reaction will result in the formation of an alkene. The double bond will form between the α-carbon (the carbon bonded to bromine) and the β-carbon from which the hydrogen is abstracted. The major product will be the more substituted alkene, following Zaitsev's rule, unless steric hindrance favors the less substituted alkene.

Step 5: Write the balanced equation. Represent the elimination reaction with the starting material, reagent, and the major product (an alkene). Ensure the equation is balanced with respect to atoms and charges. The byproduct of the reaction will be NaBr and tert-butanol (C(CH3)3OH).

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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, replacing a leaving group. In this case, the bromine atom (Br) acts as the leaving group, and the alkoxide ion (NaOC(CH₃)₃) serves as the nucleophile. Understanding this mechanism is crucial for predicting the products of the reaction.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. The presence of a chiral center in the reactant can lead to the formation of different stereoisomers in the product. Recognizing the stereochemical implications of the reaction is essential for accurately depicting the major product.

Reaction Mechanism

A reaction mechanism outlines the step-by-step process by which reactants transform into products. For this reaction, understanding the mechanism helps in predicting the major product formed after the nucleophilic attack and the subsequent steps involved. This knowledge is vital for writing a balanced equation that accurately represents the transformation.

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Related Practice

Textbook Question

For each reaction, decide whether substitution or elimination (or both) is possible, and predict the products you expect. Label the major products.

a. 1−bromo−1−methylcyclohexane + NaOH in acetone

Textbook Question

Under second-order conditions (strong base/nucleophile), S_N2 and E2 reactions may occur simultaneously and compete with each other. Show what products might be expected from the reaction of 2-bromo-3-methylbutane (a moderately hindered 2° alkyl halide) with sodium ethoxide.

Textbook Question

When (1-bromoethyl)cyclohexane is heated in methanol for an extended period of time, five products result: two ethers and three alkenes. Predict the products of this reaction, and propose mechanisms for their formation.

Textbook Question

Give the substitution and elimination products you would expect from the following reactions.

a. 3-bromo-3-ethylpentane heated in methanol

Textbook Question

If 2-fluoropentane could undergo an E1 reaction, would you expect the major product to be the more stable alkene or the less stable alkene? Explain your answer.

Textbook Question

Four alkenes are formed from the E1 reaction of 3-bromo-2,3-dimethylpentane and methanol. Draw the structures of the alkenes and rank them according to the amount that would be formed.

Textbook Question

Draw the major elimination product that would be obtained from each of the following reactants with a strong base and with a weak base:

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?

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Write a balanced equation for each reaction, showing the major product you expect.(b)

Key Concepts

Nucleophilic Substitution

Stereochemistry

Reaction Mechanism

Watch next

Write a balanced equation for each reaction, showing the major product you expect.
(b)