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

Cumulative Substitution/Elimination

Organic Chemistry

8. Elimination Reactions

Cumulative Substitution/Elimination

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3:19 minutes

Problem 64a,b

Textbook Question

After a proton is removed from the OH group, which compound in each pair forms a cyclic ether more rapidly?
a.
b.

Verified step by step guidance

Step 1: Analyze the structure of each compound in the pairs (a and b). Both compounds in each pair contain an OH group and a Cl group, which can participate in an intramolecular reaction to form a cyclic ether.

Step 2: Consider the mechanism of cyclic ether formation. This typically involves the removal of a proton from the OH group, followed by a nucleophilic attack of the oxygen on the carbon attached to the chlorine atom, leading to the formation of a cyclic ether.

Step 3: Evaluate the ring size that would be formed in each case. Smaller rings (e.g., 5- or 6-membered rings) are generally more stable due to reduced ring strain compared to larger rings.

Step 4: Compare the distance between the OH group and the Cl group in each compound. In pair (a), compound (i) forms a 5-membered ring, while compound (ii) forms a 6-membered ring. In pair (b), compound (i) forms a 4-membered ring, while compound (ii) forms a 5-membered ring.

Step 5: Based on ring stability, predict which compound in each pair forms a cyclic ether more rapidly. Compound (ii) in pair (a) is likely to form a cyclic ether more rapidly due to the stability of the 6-membered ring. Compound (ii) in pair (b) is likely to form a cyclic ether more rapidly due to the stability of the 5-membered ring compared to the 4-membered ring.

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Key Concepts

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

Cyclic Ether Formation

Cyclic ethers are formed through intramolecular reactions where a hydroxyl group (OH) reacts with a leaving group, typically resulting in the formation of a ring structure. The stability of the cyclic ether and the rate of formation depend on the sterics and electronics of the reactants, as well as the ability of the leaving group to depart effectively.

Protonation and Leaving Groups

In organic reactions, the removal of a proton from an alcohol group enhances the nucleophilicity of the oxygen atom, making it more reactive towards electrophiles. The presence of a good leaving group, such as a halide, is crucial as it facilitates the formation of the cyclic ether by allowing the nucleophile to attack and form a bond while the leaving group departs.

Steric Hindrance

Steric hindrance refers to the repulsion between bulky groups in a molecule that can impede reactions. In the context of cyclic ether formation, steric hindrance can affect the accessibility of the hydroxyl group to the electrophile, influencing the rate at which the cyclic ether is formed. Less hindered structures typically react more rapidly than those with significant steric bulk.

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Related Practice

Textbook Question

What halides would undergo E2 dehydrohalogenation to give the following pure alkenes?

a. hex-1-ene

b. isobutylene

c. pent-2-ene

Textbook Question

When the following compound is treated with sodium methoxide in methanol, two elimination products are possible. Explain why the deuterated product predominates by about a 7:1 ratio (refer to Problem 7-75).

Textbook Question

Protonation converts the hydroxy group of an alcohol to a good leaving group. Suggest a mechanism for each reaction.

(b)

Textbook Question

Draw the products of the following intramolecular reactions:

Textbook Question

cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they react with HO⁻.

c. How many stereoisomers does each of the elimination and substitution reactions form?

Textbook Question

Explain how each of the following changes affect the rate of the reaction of 1-bromobutane with ethoxide ion in DMF.

a. The concentration of both the alkyl halide and the nucleophile are tripled.

b. The solvent is changed to ethanol.

Textbook Question

Explain how the following changes affect the rate of the reaction of 2-bromo-2-methylbutane with methanol:

a. The alkyl halide is changed to 2-chloro-2-methylbutane.

b. The alkyl halide is changed to 2-chloro-3-methylbutane.

Textbook Question

The following substitution reaction, between a strong base and a 1° haloalkane, occurs in a single step via backside displacement. Yet it is not technically an S_N2 reaction. Why?

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After a proton is removed from the OH group, which compound in each pair forms a cyclic ether more rapidly? a. b.

Key Concepts

Cyclic Ether Formation

Protonation and Leaving Groups

Steric Hindrance

Watch next

After a proton is removed from the OH group, which compound in each pair forms a cyclic ether more rapidly?
a.
b.