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

Substitution Comparison

Organic Chemistry

7. Substitution Reactions

Substitution Comparison

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2:11 minutes

Problem 82c,d

Textbook Question

Fill in the squares in the following chemical equations:
c.
d.

Verified step by step guidance

Step 1: Analyze the first reaction. The starting material is cyclohexyl chloride (C6H11Cl), and the product is cyclohexyl phenyl ether (C6H11-O-C6H5). This suggests that the missing reactant in the square is phenol (C6H5OH), which reacts with cyclohexyl chloride in the presence of a base to form the ether.

Step 2: For the first reaction, the mechanism likely involves a nucleophilic substitution (SN2 or SN1) where phenol acts as the nucleophile, attacking the electrophilic carbon attached to the chlorine atom in cyclohexyl chloride.

Step 3: Analyze the second reaction. The product is a substituted cyclohexane with a methyl group and a cyano group (-C≡N) attached. This suggests that the missing reactant in the square is methylcyclohexane (C6H11CH3), which reacts with cyanide ion (CN⁻) in a substitution reaction.

Step 4: For the second reaction, the mechanism likely involves a nucleophilic substitution (SN2) where the cyanide ion attacks the electrophilic carbon in methylcyclohexane, replacing a leaving group (likely a halide such as bromine or chlorine).

Step 5: Ensure that the reaction conditions for both reactions are appropriate. For the first reaction, a base like NaOH or KOH may be required to deprotonate phenol and enhance its nucleophilicity. For the second reaction, polar aprotic solvents like DMSO or acetone may be used to facilitate the SN2 mechanism.

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Key Concepts

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

Balancing Chemical Equations

Balancing chemical equations is essential in organic chemistry as it ensures that the number of atoms for each element is the same on both sides of the equation. This reflects the law of conservation of mass, which states that matter cannot be created or destroyed in a chemical reaction. Understanding how to balance equations involves identifying reactants and products, and adjusting coefficients to achieve equilibrium.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In organic chemistry, recognizing functional groups is crucial for predicting the behavior of compounds during reactions. Common functional groups include hydroxyl (-OH), carboxyl (-COOH), and amine (-NH2), each imparting distinct properties and reactivity to the organic molecules they are part of.

Reaction Mechanisms

Reaction mechanisms describe the step-by-step process by which reactants are converted into products in a chemical reaction. Understanding these mechanisms is vital for predicting the outcome of reactions and for designing new synthetic pathways in organic chemistry. Key concepts include nucleophiles, electrophiles, and intermediates, which help explain how bonds are formed and broken during the reaction.

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Related Practice

Textbook Question

Predict the product of the following substitution reactions, paying close attention to the stereochemical outcome of the reactions.

(b)

Textbook Question

Predict the product of the following substitution reactions, paying close attention to the stereochemical outcome of the reactions.

(c)

Textbook Question

Would the following nucleophiles be more likely to participate in an S_N1 or S_N2 reaction?

(e) H₂O

Textbook Question

Fill in the squares in the following chemical equations:

Textbook Question

What substitution products are obtained when each of the following compounds is added to a solution of sodium acetate in acetic acid?

a. 2-chloro-2-methyl-3-hexene

b. 3-bromo-1-methylcyclohexene

Textbook Question

Draw the substitution products for each of the following S_N2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed:

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

b. (3S,4R)-3-bromo-4-methylhexane + CH₃O^-

Textbook Question

Draw the substitution products for each of the following S_N2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed:

c. (3R,4R)-3-bromo-4-methylhexane + CH₃O^-

d. (3R,4S)-3-bromo-4-methylhexane + CH₃O^-

Textbook Question

Propose a mechanism for the following reaction.

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