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a. Which compounds are Br酶nsted-Lowry acids: \(\mathrm{HBr}, \mathrm{NH}_{3}, \mathrm{CCl}_{4} ?\) b. Which compounds are Br酶nsted-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
a. HBr is an acid; b. (CH鈧)鈧僀O鈦 is a base; c. CH鈧僀H鈧侽H is both, others are neither.

Step by step solution

01

Understanding Br酶nsted-Lowry Acids

A Br酶nsted-Lowry acid is a species that donates a proton (H鈦) in a reaction. To identify the acids from the given list, we need to consider which compounds can donate a proton.
02

Identifying Acid: HBr

HBr is a hydrogen halide and is known to dissociate in water to donate a proton, forming H鈦 and Br鈦. Therefore, HBr acts as a Br酶nsted-Lowry acid.
03

Analyzing NH鈧 as an Acid

NH鈧, or ammonia, typically accepts protons rather than donating them because of the lone pair on nitrogen. It is more commonly a base than an acid under Br酶nsted-Lowry theory.
04

Analyzing CCl鈧 as an Acid

CCl鈧 is a covalent compound with no hydrogen atoms to donate as protons. Hence, it cannot act as a Br酶nsted-Lowry acid.
05

Conclusion for Part a

From the list, only HBr acts as a Br酶nsted-Lowry acid.
06

Understanding Br酶nsted-Lowry Bases

A Br酶nsted-Lowry base is a species that accepts a proton (H鈦) in a reaction. To identify the bases, we need to determine which compounds have the ability to accept protons.
07

Analyzing CH鈧僀H鈧 as a Base

CH鈧僀H鈧 (ethane) is an alkane and does not have any lone pairs or resonance structures capable of accepting protons. It cannot act as a Br酶nsted-Lowry base.
08

Identifying Base: (CH鈧)鈧僀O鈦

(CH鈧)鈧僀O鈦 is an alkoxide ion with a lone pair on the oxygen, making it able to accept a proton, thus acting as a Br酶nsted-Lowry base.
09

Analyzing HC鈮H as a Base

HC鈮H, known as acetylene, can lose a proton to form its conjugate base, but its ability to gain a proton is limited. It is relatively acidic compared to other hydrocarbons, but not a strong base.
10

Conclusion for Part b

From the list, only (CH鈧)鈧僀O鈦 acts as a Br酶nsted-Lowry base.
11

Classifying CH鈧僀H鈧侽H

CH鈧僀H鈧侽H (ethanol) can act as both an acid and a base. It can donate a proton from its -OH group, behaving as an acid, or accept a proton via lone pairs on the oxygen, behaving as a base.
12

Classifying CH鈧僀H鈧侰H鈧侰H鈧

CH鈧僀H鈧侰H鈧侰H鈧 (butane) is a simple alkane, lacking the functional groups needed to act as a Br酶nsted-Lowry acid or base.
13

Classifying CH鈧僀O鈧侰H鈧

CH鈧僀O鈧侰H鈧 (methyl acetate) does not easily donate or accept protons, so under typical conditions, it does not function as a Br酶nsted-Lowry acid or base.
14

Conclusion for Part c

Ethanol (CH鈧僀H鈧侽H) can act as both an acid and a base, butane (CH鈧僀H鈧侰H鈧侰H鈧) and methyl acetate (CH鈧僀O鈧侰H鈧) do not act as acids or bases.

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Key Concepts

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

Proton Donor
In the Br酶nsted-Lowry Acid-Base Theory, a **proton donor** refers to a species that can release a proton, represented as (H鈦), in a chemical reaction. This theory is foundational for understanding acids, as it broadens the definition beyond just aqueous solutions.

In the context of the exercise, compounds like (HBr) exhibit these characteristics. When dissolved in water, (HBr) donates (H鈦), breaking into (H鈦) and (Br鈦), thus acting as a Br酶nsted-Lowry acid.

A proton donor doesn't need to be in water to act as an acid; it just needs to be capable of releasing a proton within any chemical interaction.
  • **Ability to Donate Protons:** Central to its classification as a proton donor.
  • **Presence of Hydrogens:** Compounds considered as acids must have hydrogen atoms available for donation.
Understanding which chemicals release protons can help identify acids in reactions beyond typical watery environments.
Proton Acceptor
The concept of a **proton acceptor** is equally vital in the Br酶nsted-Lowry framework. Substances that serve as proton acceptors are typically referred to as bases. These are species that can attract and bind with a proton ( (H鈦)) during a chemical reaction.

("(CH鈧)鈧僀O鈦"), known as an alkoxide ion, unequivocally illustrates this concept as it contains a lone pair on its oxygen atom, enabling it to accept a proton efficiently.

An important aspect when considering proton acceptors is the presence of lone pairs or negative charges capable of bonding with protons.
  • **Lone Pair Electrons:** Essential for the acceptance of protons.
  • **Affinity for Protons:** Determines the strength of a base.
These factors make bases adept at neutralizing acids by coupling with their proton releases.
Acid-Base Classification
In Br酶nsted-Lowry theory, **acid-base classification** provides the framework to categorize substances based on their interactions with protons.

An important case is **ethanol (CH鈧僀H鈧侽H)**, which can either donate a proton, making it an acid, or accept a proton at the oxygen's lone pairs, thus functioning as a base. This dual potential shows that some substances don't fit neatly into just one category.

Other compounds like **butane (CH鈧僀H鈧侰H鈧侰H鈧)** show neither propensity, as they lack the functional groups to donate or accept protons, categorically excluding them from being either acids or bases.

Here are critical distinctions in classifying:
  • **Proton Donating Ability:** To identify acids.
  • **Proton Accepting Ability:** To determine bases.
  • **Functional Group Presence:** Critical in evaluating the compound's behavior as an acid, base, or neutral.
Such classifications are pivotal in predicting and understanding chemical reactions and the roles individual compounds will play.

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Most popular questions from this chapter

Which compound in each pair of isomers is the stronger acid? a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) or \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{3}\) or \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\)

Dimethyl ether \(\left(\mathrm{CH}_{3} \mathrm{OCH}_{3}\right)\) and ethanol \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\right)\) are isomers, but \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) has a \(\mathrm{pK}_{\mathrm{a}}\) of 40 and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) has a \(\mathrm{pK}_{\mathrm{a}}\) of 16 . Why are these \(\mathrm{pK}_{\mathrm{a}}\) values so different?

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. \(\mathrm{CH}_{2}=\mathrm{CH}_{2}, \mathrm{HC} \equiv \mathrm{CH}, \mathrm{CH}_{4}\)

Rank the compounds in each group in order of increasing acidity. a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\) b. \(\mathrm{BrCH}_{2} \mathrm{COOH}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2},\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)

What is \(K_{\mathrm{a}}\) for each compound? Use a calculator when necessary. a. \(\quad \mathrm{H}_{2} \mathrm{~S}\) b. \(\mathrm{Cl} \mathrm{CH}_{2} \mathrm{COOH}\) C. \(\quad \mathrm{HCN}\) \(\mathrm{pK}_{\mathrm{a}}=7.0\) \(\mathrm{pK}_{\mathrm{a}}=2.8\) \(\mathrm{pK}_{\mathrm{a}}=9.1\)

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