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

Previous problemNext problem

2:26 minutes

Problem 42g,h

Textbook Question

Predict the products of the following acid–base reactions.
(g) HCOOH + CH₃O^– ⇌
(h) ⁺NH₃CH₂COOH + 2 ^–OH ⇌

Verified step by step guidance

Step 1: Identify the acid and base in each reaction. In reaction (g), HCOOH (formic acid) is the acid, and CH3O- (methoxide ion) is the base. In reaction (h), +NH3CH2COOH (aminoacetic acid) is the acid, and -OH (hydroxide ion) is the base.

Step 2: Determine the conjugate base and conjugate acid formed in each reaction. For reaction (g), the acid HCOOH will donate a proton (H+) to the base CH3O-, forming HCOO- (formate ion) and CH3OH (methanol). For reaction (h), the acid +NH3CH2COOH will donate a proton to the base -OH, forming NH2CH2COO- (glycinate ion) and H2O (water).

Step 3: Write the balanced chemical equation for each reaction. For reaction (g), the equation is:

{HCOOH}_{+} {CH 3_{O}}_{-} ⇌ {HCOO}_{-} + CH 3_{OH}

. For reaction (h), the equation is:

+ NH 3_{CH 2_{COOH}} + 2 - OH ⇌ {NH 2_{CH 2_{COO}} -}_{+ H 2_{O}}

Step 4: Consider the equilibrium position of each reaction. The position of equilibrium depends on the relative strengths of the acids and bases involved. Stronger acids and bases will drive the equilibrium towards the formation of weaker conjugate acids and bases.

Step 5: Verify the stability of the products formed. Ensure that the products are stable and make sense chemically. For example, methanol and water are stable products in their respective reactions, and the conjugate bases formed are reasonable given the starting materials.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Acid-Base Reaction

An acid-base reaction involves the transfer of a proton (H+) from an acid to a base. In organic chemistry, this often results in the formation of a conjugate acid and a conjugate base. Understanding the strength and structure of acids and bases helps predict the direction and products of the reaction.

Conjugate Acid-Base Pairs

Conjugate acid-base pairs are related by the gain or loss of a proton. When an acid donates a proton, it forms its conjugate base, and when a base accepts a proton, it forms its conjugate acid. Identifying these pairs is crucial for predicting the products of acid-base reactions.

pKa and Reaction Direction

The pKa value indicates the strength of an acid; lower pKa values mean stronger acids. In acid-base reactions, the equilibrium favors the formation of the weaker acid and base. Comparing the pKa values of the reactants and products helps determine the direction and extent of the reaction.

Watch next

Master The Lewis definition of acids and bases. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

The following compounds can all react as acids.

a. For each compound, show its conjugate base. Show any resonance forms if applicable.

Textbook Question

Oxidation of a primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

(a) Show how you would use acid–base extraction to purify the pentanal.

(b) Which of the expected impurities cannot be removed from pentanal by acid–base extractions? How would you remove this impurity?

Textbook Question

The boiling points of hex-1-ene (64 °C) and hex-1-yne (71 °C) are sufficiently close that it is difficult to achieve a clean separation by distillation. Show how you might use the acidity of hex-1-yne to remove the last trace of it from a sample of hex-1-ene.

Textbook Question

The following compounds can all react as bases.

a. For each compound, show its conjugate acid. Show any resonance forms if applicable.

Textbook Question

Sulfuric acid is a very strong acid. Show how the following equation can be used to explain that sulfuric acid is at once an Arrhenius, Brønsted–Lowry, and Lewis acid.

Multiple Choice

Which of the following factors does not affect the acidity of a compound?

Multiple Choice

Which of the following is a characteristic of a strong acid in aqueous solution?

Multiple Choice

In the context of acid-base chemistry, what is a negative control?

Show more practices