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Chapter 2: Problem 1

a. Which compounds are Bronsted-Lowry acids: \(\mathrm{HBr}, \mathrm{NH}_{3}, \mathrm{CCl}_{4}\) ? b. Which compounds are Bronsted-Lowry bases: \(\mathrm{CH}_{3} \mathrm{CH}_{3},\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CO}^{-}, \mathrm{HC} \equiv \mathrm{CH}\) ? c. Classify each compound as an acid, a base, or both: \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}, \mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{CH}_{3}\).

Short Answer

Expert verified
HBr is a Bronsted-Lowry acid; (CH鈧�)鈧僀O鈦� is a base; CH鈧僀H鈧侽H is both an acid and a base.

Step by step solution

01

Understanding Bronsted-Lowry Acids

A Bronsted-Lowry acid is a substance that can donate a proton (H鈦�) to another substance. We need to identify which compounds have hydrogen atoms that can be donated as a proton.
02

Identifying Bronsted-Lowry Acids

Among the given compounds, \(\mathrm{HBr}\) has a hydrogen atom that can be easily donated. Therefore, \(\mathrm{HBr}\) is a Bronsted-Lowry acid. \(\mathrm{NH}_{3}\) and \(\mathrm{CCl}_{4}\) do not donate protons typically, so they are not considered Bronsted-Lowry acids.
03

Understanding Bronsted-Lowry Bases

A Bronsted-Lowry base is a substance that can accept a proton (H鈦�) from another substance. We need to identify which compounds have lone pairs of electrons or negative charges that can accept a proton.
04

Identifying Bronsted-Lowry Bases

Among the given compounds, \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CO}^{-}\) has a negative charge that can accept a proton, making it a Bronsted-Lowry base. \(\mathrm{CH}_{3}\mathrm{CH}_{3}\) and \(\mathrm{HC} \equiv \mathrm{CH}\) do not have characteristics typical of a Bronsted-Lowry base.
05

Classifying Each Compound

For \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{OH}\) (ethanol), it can donate a proton from the hydroxyl group, acting as a Bronsted-Lowry acid, and it also has a lone pair on the oxygen, which can accept a proton, making it both an acid and a base. \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{CH}_{2}\mathrm{CH}_{3}\) (butane) cannot act as an acid or base in the Bronsted-Lowry sense. \(\mathrm{CH}_{3}\mathrm{CO}_{2}\mathrm{CH}_{3}\) (methyl acetate) does not have easily assessible protons to donate nor lone pairs that can accept protons readily, so it is neither a Bronsted-Lowry acid nor base.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Bronsted-Lowry acids
In the Bronsted-Lowry theory, an acid is a molecule or ion that can donate a proton, which is often a hydrogen ion (H鈦�), to another substance. This concept is crucial in understanding the behavior of acids in a chemical reaction.

Here鈥檚 how you can identify a Bronsted-Lowry acid:
  • Look for compounds containing hydrogen atoms (H).
  • The hydrogen must be able to "leave" the compound as a proton.
  • Typically, the stronger the acid, the easier it is to donate this proton.
Therefore, among the given compounds
  • HBr is considered a strong Bronsted-Lowry acid as it can easily donate a hydrogen ion.
  • NH鈧� and CCl鈧�, on the other hand, are not bronsted-lowry acids as they do not readily release protons.
Understanding which compounds can donate a proton is fundamental to predicting how a chemical will react under different conditions.
Bronsted-Lowry bases
In the Bronsted-Lowry framework, bases are substances that have the ability to accept a proton. This could mean possessing a negative charge or having lone pairs of electrons that can form bonds with protons. Identifying a base can be straightforward when you understand the typical characteristics to look for:

  • Compounds with a negative charge are likely candidates for being Bronsted-Lowry bases.
  • Presence of lone pairs of electrons that can attract a proton.
In our examples:
  • (CH鈧�)鈧僀O鈦� is a Bronsted-Lowry base as it has a negative charge that can readily accept a proton.
  • CH鈧僀H鈧� and HC鈮H do not possess significant electron pairs or charges to accept a proton.
Understanding Bronsted-Lowry bases helps predict how molecules will behave when they come in contact with acids, specifically in neutralization reactions.
Proton donation and acceptance
Proton donation and acceptance are at the heart of Bronsted-Lowry theory. When dealing with chemical reactions, these processes define how acids and bases interact.

Let's break down the main points:
  • A Bronsted-Lowry acid donates a proton (H鈦�).
  • A Bronsted-Lowry base accepts a proton.
The ability of a compound to either donate or accept a proton can label it as a specific category in the acid-base spectrum. In some cases, certain compounds can act as both donor and acceptor:
  • Ethanol (CH鈧僀H鈧侽H) can donate a proton through its hydroxyl group and accept a proton at the same location due to the lone pairs on oxygen, making it an amphoteric molecule (both acid and base).
  • Other compounds like butane (CH鈧僀H鈧侰H鈧侰H鈧�) are neither because they do not readily donate or accept protons.
  • Methyl acetate (CH鈧僀O鈧侰H鈧�) does not easily engage in proton transfer.
By mastering these concepts of proton donation and acceptance, you gain a better understanding of reaction dynamics and how chemical behaviors are influenced by the presence of acids and bases.

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Most popular questions from this chapter

Hydroxide (OH) can react as a Bronsted-Lowry base (and remove a proton), or a Lewis base (and attack a carbon atom). (a) What organic product is formed when "OH reacts with the carbocation \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}^{+}\) as a Bronsted-Lowry base? (b) What organic product is formed when "OH reacts with \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}^{+}\) as a Lewis base?

Which compound in each pair is the stronger acid? a. \(\mathrm{CICH}_{2} \mathrm{COOH}\) and \(\mathrm{FCH}_{2} \mathrm{COOH}\) c. \(\mathrm{CH}_{3} \mathrm{COOH}\) and \(\mathrm{O}_{2} \mathrm{NCH}_{2} \mathrm{COOH}\) b. \(\mathrm{Cl}_{2} \mathrm{CHCH}_{2} \mathrm{OH}\) and \(\mathrm{Cl}_{2} \mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{OH}\)

Rank the conjugate bases of each group of acids in order of increasing basicity. a. \(\mathrm{NH}_{3}, \mathrm{H}_{2} \mathrm{O}, \mathrm{CH}_{4}\) b. \(\mathrm{CH}_{2}=\mathrm{CH}_{2}, \mathrm{HC} \equiv \mathrm{CH}, \mathrm{CH}_{4}\)

What is the conjugate acid of each base? a. \(\mathrm{H}_{2} \mathrm{O}\) b. \(\mathrm{NH}_{2}\) c. \(\mathrm{HCO}_{3}^{-}\) d. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NHCH}_{3}\) e. \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) f. \(\mathrm{CH}_{3} \mathrm{COO}^{-}\)

Draw the products of each reaction and determine the direction of equilibrium. \(\mathrm{a} . \mathrm{H}-\mathrm{CmC}-\mathrm{H}+\mathrm{H}^{-}\) c. \(\mathrm{CH}_{3} \mathrm{COOH}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-}\) b. \(\mathrm{CH}_{4}+\mathrm{OH}\) d. \(\mathrm{Cl}^{-}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)
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