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

10. Addition Reactions

Addition Reaction

Organic Chemistry

10. Addition Reactions

Addition Reaction

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3:04 minutes

Problem 36a,b,c

Textbook Question

Predict the products formed when CH₃CH₂–C≡C:^–Na⁺ reacts with the following compounds.
a. ethyl bromide
b. tert-butyl bromide
c. formaldehyde

Verified step by step guidance

Step 1: Analyze the structure of the given reactant in the image. Determine its functional groups, nucleophilicity, and electrophilicity. This will help predict how it interacts with the given compounds.

Step 2: For (a) ethyl bromide, identify the type of reaction that can occur. Ethyl bromide is a primary alkyl halide, which typically undergoes nucleophilic substitution (SN2 mechanism) with a strong nucleophile. Consider the reactant's nucleophilic site and predict the substitution product.

Step 3: For (b) tert-butyl bromide, recognize that it is a tertiary alkyl halide. Tertiary alkyl halides favor nucleophilic substitution via the SN1 mechanism due to steric hindrance. Predict the formation of a carbocation intermediate and the subsequent product based on the reactant's nucleophilic site.

Step 4: For (c) formaldehyde, understand that formaldehyde is an electrophile due to the partial positive charge on the carbon atom. The reactant's nucleophilic site will attack the carbonyl carbon, leading to the formation of an addition product. Predict the structure of the product based on this interaction.

Step 5: Summarize the predicted products for each reaction, ensuring that stereochemistry, regiochemistry, and reaction mechanisms are considered where applicable. This will provide a comprehensive understanding of the outcomes for each compound.

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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 replaces a leaving group in a molecule. This process can occur via two main mechanisms: SN1, which involves a two-step process with carbocation formation, and SN2, which is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs. Understanding these mechanisms is crucial for predicting the products of reactions involving alkyl halides like ethyl and tert-butyl bromide.

Reactivity of Alkyl Halides

Alkyl halides, such as ethyl bromide and tert-butyl bromide, vary in their reactivity based on their structure. Primary alkyl halides (like ethyl bromide) typically undergo SN2 reactions due to steric accessibility, while tertiary alkyl halides (like tert-butyl bromide) favor SN1 reactions due to the stability of the resulting carbocation. Recognizing these differences is essential for predicting the outcome of reactions with these compounds.

Carbonyl Chemistry

Formaldehyde is a simple carbonyl compound that can undergo nucleophilic addition reactions. In these reactions, nucleophiles attack the electrophilic carbon of the carbonyl group, leading to the formation of alcohols or other derivatives. Understanding the behavior of carbonyl compounds is vital for predicting the products when they react with nucleophiles, such as those generated from alkyl halides.

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Related Practice

Textbook Question

Starting with ethyne, describe how the following compounds can be synthesized:

a. (3S,4R)-4-bromo-3-hexanol and (3R,4S)-4-bromo-3-hexanol

Multiple Choice

Predict the major organic product of the following reaction.

Textbook Question

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(g)

Textbook Question

Using any necessary inorganic reagents, show how you would convert acetylene and isobutyl bromide to

(a) meso-2,7-dimethyloctane-4,5-diol, (CH₃)₂CHCH₂CH(OH)CH(OH)CH₂CH(CH₃)₂.

Textbook Question

Show how you would accomplish the following synthetic conversions.

c. 1-methylcyclopentanol → 2-chloro-1-methylcyclopentanol

Problem-Solving Hint: The opening of a halonium ion is driven by its electrophilic nature. The weak nucleophile attacks the carbon bearing more positive charge.

Textbook Question

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(h)

Textbook Question

Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.

(a)

Textbook Question

Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.

(c)

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Predict the products formed when CH3CH2–C≡C:–Na+ reacts with the following compounds.a. ethyl bromideb. tert-butyl bromidec. formaldehyde

Key Concepts

Nucleophilic Substitution

Reactivity of Alkyl Halides

Carbonyl Chemistry

Watch next

Predict the products formed when CH₃CH₂–C≡C:^–Na⁺ reacts with the following compounds.
a. ethyl bromide
b. tert-butyl bromide
c. formaldehyde