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Textbook Question
Chapter 2, Problem 2.1P

a. Which compounds are Bronsted-Lowry acids: HBr, NH 3 , CCl 4 ?

b. Which compounds are Bronsted-Lowry bases: CH 3 CH 3 ( CH 3 ) 3 CO , HC CH ?

c. Classify each compound as an acid, a base, or both:

CH 3 CH 2 OH, CH 3 CH 2 CH 2 CH 3 , CH 3 CO 2 CH 3 .

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: Among the given compounds, Bronsted-Lowry acids are to be identified.

Concept introduction: Bronsted-Lowry acids are those species which donate proton. They are also known as proton donor. The net charge on Bronsted-Lowry acids can be zero or negative or positive.

Answer to Problem 2.1P

The Bronsted-Lowry acid is HBr.

Explanation of Solution

All Bronsted-Lowry acids donate proton.

Hydrogen bromide contain hydrogen atom. Hence, it is a Bronsted-Lowry acid.

Ammonia contains a lone pair of electrons which can be easily donated to form a new bond. Hence, it is a Bronsted-Lowry base.

No hydrogen is present in the CCl4. Hence, it is not a Bronsted-Lowry acid.

Conclusion

In the given set of compounds, Bronsted-Lowry acid is HBr.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: Among the given compounds, Bronsted-Lowry bases are to be identified.

Concept introduction: Bronsted-Lowry bases are those species which can accept a proton. The Base must contain a lone pair or pi bond that could be easily donated to an acid to form a new bond. Bronsted-Lowry base are proton acceptor. The net charge on Bronsted-Lowry base can be zero and negative.

Answer to Problem 2.1P

The Bronsted-Lowry acids are CHCH and (CH3)3CO.

Explanation of Solution

All Bronsted-lowry bases contain lone pair of electrons or pi bond. In (CH3)3CO, oxygen atom possess negative charge. It means that it can accept a proton. Hence, (CH3)3CO is a Bronsted-Lowry base.

Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card, Chapter 2, Problem 2.1P , additional homework tip  1

Figure 1

The molecule HCCH contains pi bonds. Hence, HCCH is a Bronsted-Lowry base.

Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card, Chapter 2, Problem 2.1P , additional homework tip  2

Figure 2

There is neither a pi bond nor a negative charge present in CH3CH3. Hence, it is not a Bronsted-Lowry base.

Conclusion

In the given set of compounds, Bronsted-Lowry acids are CHCH and (CH3)3CO.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: Among the given compounds, Bronsted-lowry bases are to be identified.

Concept introduction: Bronsted-Lowry bases are those species which can accept a proton. The Base must contain a lone pair or pi bond that could be easily donated to an acid to form a new bond. Bronsted-Lowry base are proton acceptor. The net charge on Bronsted-Lowry base can be zero and negative.

Answer to Problem 2.1P

The Bronsted-Lowry acids are CH3CH2CH2CH3. The compounds which are both Bronsted-Lowry acid and Bronsted-Lowry base are CH3CH2OH, CH3COOCH3.

Explanation of Solution

All Bronsted-Lowry bases contain lone pairs of electrons or pi bond. Bronsted-Lowry acids contain proton.

Ethanol contains hydrogen atom and lone pairs on oxygen atom. Hence, it is a Bronsted-Lowry base as well as a Bronsted-Lowry acid.

Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card, Chapter 2, Problem 2.1P , additional homework tip  3

Figure 3

Propane contains only hydrogen atoms. Hence, it is a Bronsted-Lowry acid.

Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card, Chapter 2, Problem 2.1P , additional homework tip  4

Figure 4

CH3COOCH3 contains hydrogen atom and lone pairs on oxygen atom. Hence, it is a Bronsted-Lowry base as well as a Bronsted-Lowry acid.

Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card, Chapter 2, Problem 2.1P , additional homework tip  5

Figure 5

Conclusion

The Bronsted-Lowry acids are CH3CH2CH2CH3. The compounds which are both Bronsted-Lowry acid and Bronsted-Lowry bases are CH3CH2OH, CH3COOCH3.

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a. Which compounds are Bronsted-Lowry acids: HBr, NH3, CCl4?b. Which compounds are Bronsted-Lowry bases: CH3CH3, (CH3)3CO-, CH =_CH ?c. Classify each compound as an acid, a base, or both: CH3CH2OH, CH3CH2CH2CH3, CH3CO2CH3
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Chapter 2 Solutions

Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card

Ch. 2 - Prob. 2.11PCh. 2 - Draw the products of each reaction and determine...Ch. 2 - Prob. 2.13PCh. 2 - Without reference to a pKa table, decide which...Ch. 2 - Rank the labeled H atoms in the following compound...Ch. 2 - Which hydrogen in each molecule is most...Ch. 2 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2 - Which compound in each pair of isomers is the...Ch. 2 - Which compound in each pair is the stronger acid?...Ch. 2 - Glycolic acid, HOCH2CO2H, is the simplest member...Ch. 2 - Explain the apparent paradox. HBr is a stronger...Ch. 2 - The CH bond in acetone, (CH3)2C=O, has a pKa of...Ch. 2 - Acetonitrile (CH3CN) has a pKa of 25, making it...Ch. 2 - For each pair of compounds: [1] Which indicated H...Ch. 2 - Rank the compounds in each group in order of...Ch. 2 - Which proton in each of the following drugs is...Ch. 2 - Which anion A or B is the stronger base? ABCh. 2 - Prob. 2.28PCh. 2 - Problem 2.29 Compounds like amphetamine that...Ch. 2 - Problem 2.30 Which species are Lewis bases? a. b....Ch. 2 - Which species are Lewis acids? a. b. c. d. Ch. 2 - For each reaction, label the Lewis acid and base....Ch. 2 - Prob. 2.33PCh. 2 - Prob. 2.34PCh. 2 - Label the Lewis acid and base. Use curved arrow...Ch. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - 2.38 What is the conjugate acid of each base? a....Ch. 2 - 2.39 What is the conjugate base of each acid? a....Ch. 2 - 2.40 Draw the products formed from the acid-base...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Draw the products of each proton transfer...Ch. 2 - Prob. 2.43PCh. 2 - Prob. 2.44PCh. 2 - What is Ka for each compound? Use a calculator...Ch. 2 - What is the pKa for each compound? a. b. c.Ch. 2 - Which of the following bases are strong enough to...Ch. 2 - Which compounds can be deprotonated by OH, so that...Ch. 2 - Draw the products of each reaction. Use the pKa...Ch. 2 - Rank the following compounds in order of...Ch. 2 - 2.51 Rank the following ions in order of...Ch. 2 - Prob. 2.52PCh. 2 - Prob. 2.53PCh. 2 - 2.54 The of three bonds is given below. a. For...Ch. 2 - a. What is the conjugate acid of A? b. What is the...Ch. 2 - 2.56 Draw the structure of a constitutional isomer...Ch. 2 - 2.57 Many drugs are Bronsted-Lowry acids or...Ch. 2 - Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH)...Ch. 2 - 2.59 Atenolol is a (beta) blocker, a drug used to...Ch. 2 - 2.60 Use the principles in Section 2.5 to label...Ch. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 2.62PCh. 2 - 2.63 Classify each compound as a Lewis base, a...Ch. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Label the Lewis acid and Lewis base in each...Ch. 2 - 2.66 Draw the products of each Lewis acid-base...Ch. 2 - Prob. 2.67PCh. 2 - 2.68 Answer the following questions about the four...Ch. 2 - Prob. 2.69PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - 2.72 DBU, is a base we will encounter in...Ch. 2 - 2.73 Molecules like acetamide can be protonated...Ch. 2 - Prob. 2.74PCh. 2 - Prob. 2.75PCh. 2 - 2.76 Write a stepwise reaction sequence using...Ch. 2 - Prob. 2.77PCh. 2 - 2.78 Which compound, M or N, is the stronger acid?...
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