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

3. Acids and Bases

Acids and Bases

Organic Chemistry

3. Acids and Bases

Acids and Bases

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1:17 minutes

Problem 66a

Textbook Question

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(a)

Verified step by step guidance

Step 1: Identify the functional groups in the molecule. The molecule contains a terminal alkyne (-C≡CH) and an alcohol (-OH) group.

Step 2: Recognize the reactivity of the functional groups with a strong base. A strong base can deprotonate acidic hydrogens. Terminal alkynes have acidic hydrogens due to the sp-hybridized carbon, and alcohols can also be deprotonated, but the terminal alkyne hydrogen is more acidic.

Step 3: Determine which hydrogen will be removed. The terminal alkyne hydrogen is more acidic (pKa ~25) compared to the alcohol hydrogen (pKa ~16), so the base will preferentially deprotonate the terminal alkyne.

Step 4: Write the product of the reaction. Deprotonation of the terminal alkyne will result in the formation of an alkynide ion (R-C≡C⁻), where R represents the rest of the molecule.

Step 5: Consider the stability of the product. The alkynide ion is stabilized by the strong base, and no further reaction occurs unless additional reagents are introduced.

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Key Concepts

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

Strong Bases in Organic Chemistry

Strong bases, such as sodium hydroxide (NaOH) or potassium tert-butoxide (KOtBu), are capable of deprotonating weak acids, including alcohols. In organic reactions, they can facilitate the formation of alkoxides by removing a proton from the hydroxyl (-OH) group, leading to increased nucleophilicity and reactivity of the resulting alkoxide.

Deprotonation Mechanism

Deprotonation is the process where a proton (H+) is removed from a molecule, often resulting in the formation of a negatively charged species. In the context of alcohols reacting with strong bases, the base abstracts the proton from the hydroxyl group, converting the alcohol into an alkoxide ion, which can then participate in further reactions, such as nucleophilic substitution or elimination.

Reaction Products of Alcohols with Bases

When an alcohol reacts with a strong base, the primary product is typically an alkoxide ion. Depending on the structure of the alcohol and the reaction conditions, this alkoxide can further react with electrophiles or participate in elimination reactions, leading to the formation of alkenes or other functional groups. Understanding the structure of the starting material is crucial for predicting the specific products formed.

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Related Practice

Textbook Question

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(d)

Textbook Question

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(c)

Textbook Question

Provide an arrow-pushing mechanism for the following acid–base reactions.

(d)

Textbook Question

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(b)

Textbook Question

In the following reactions,

(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and

(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]

(c)

Textbook Question

In the following reactions,

(i) identify the acid and base,

(ii) identify the most electron-rich atom in the base,

(iii) identify the most acidic hydrogen in the acid,

(c)

Textbook Question

In the following reactions,

(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and

(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]

(b)

Textbook Question

In the following reactions,

(i) identify the acid and base,

(ii) identify the most electron-rich atom in the base,

(iii) identify the most acidic hydrogen in the acid,

(b)

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For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.(a)

Key Concepts

Strong Bases in Organic Chemistry

Deprotonation Mechanism

Reaction Products of Alcohols with Bases

Watch next

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(a)