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

SN2 Reaction

Organic Chemistry

7. Substitution Reactions

SN2 Reaction

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6:00 minutes

Problem 81b

Textbook Question

Cardura, a drug used to treat hypertension, is synthesized as shown here.

b. Show the mechanism for conversion of A to B. Which is formed more rapidly, A or B?

Verified step by step guidance

Step 1: Begin by analyzing the reaction from A to B. The conversion involves the use of KOH, which is a strong base. This suggests that the reaction mechanism likely involves deprotonation or nucleophilic substitution.

Step 2: Identify the functional groups in compound A. Look for reactive sites such as hydroxyl groups, halides, or acidic hydrogens that could interact with KOH.

Step 3: Propose the mechanism. If compound A contains an acidic hydrogen, KOH will deprotonate it, forming a negatively charged intermediate. Alternatively, if A contains a halide, KOH could act as a nucleophile, displacing the halide via an SN2 mechanism.

Step 4: Compare the formation rates of A and B. The rate of formation depends on the stability of the intermediates and the activation energy of the reaction. Typically, the compound with a more stable intermediate or lower activation energy will form more rapidly.

Step 5: Consider steric and electronic effects. If compound B is sterically hindered or electronically less favorable, it may form more slowly than A. Conversely, if B is stabilized by resonance or other factors, it may form more rapidly.

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Key Concepts

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

Nucleophilic Substitution Mechanism

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, replacing a leaving group. This mechanism can occur via two main pathways: SN1, which involves a two-step process with a carbocation intermediate, and SN2, which is a one-step process where the nucleophile attacks the electrophile simultaneously as the leaving group departs. Understanding this mechanism is crucial for analyzing the conversion of compound A to B.

Reaction Conditions and Their Effects

The conditions under which a reaction occurs, such as temperature, solvent, and the presence of catalysts, significantly influence the rate and outcome of chemical reactions. In the case of converting A to B, the use of KOH suggests a strong base that can facilitate deprotonation or promote nucleophilic attack. Recognizing how these conditions affect the reaction pathway helps in predicting which compound forms more rapidly.

Kinetics of Reaction

Reaction kinetics studies the rates of chemical reactions and the factors that influence them. The rate of formation of products A and B can be determined by analyzing the energy barriers and transition states involved in their formation. In this context, understanding the kinetics will help determine which compound is formed more rapidly, providing insight into the efficiency of the synthesis process.

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Related Practice

Textbook Question

For each pair, choose the haloalkane that would react most quickly in an S_N2 reaction.

(b)

Textbook Question

For each pair, choose the haloalkane that would react most quickly in an S_N2 reaction.

(d)

Textbook Question

The following reaction, though run under standard solvolysis conditions, occurs via an S_N2 reaction. Why?

Textbook Question

Crown ethers are able to solvate cations based on their size. Specifically, 15-crown-5 forms stable complexes with sodium. How would the addition of a crown ether change the rate of an S_N2 reaction?

Textbook Question

Propose a mechanism for the following reaction that explains why the configuration of the asymmetric center in the reactant is retained in the product:

Textbook Question

The S_N2 reaction is the concerted, backside displacement of a good leaving group by a nucleophile. Why do nucleophiles attack from the back in S_N2 reactions?

Textbook Question

For each pair, choose the haloalkane that would react most quickly in an S_N2 reaction.

(a)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; If no reaction occurs, write 'no reaction.'

(f)

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Cardura, a drug used to treat hypertension, is synthesized as shown here.b. Show the mechanism for conversion of A to B. Which is formed more rapidly, A or B?

Key Concepts

Nucleophilic Substitution Mechanism

Reaction Conditions and Their Effects

Kinetics of Reaction

Watch next

Cardura, a drug used to treat hypertension, is synthesized as shown here.

b. Show the mechanism for conversion of A to B. Which is formed more rapidly, A or B?