ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 2, Problem 2.67P
Interpretation Introduction

(a)

Interpretation: The product formed by the reaction of Lewis acid (CH3CH2)3C+ with the given Lewis base is to be drawn.

Concept introduction: Lewis acid accepts an electron pair. It acts as an electrophile as it is electron deficient. Lewis base donates an electron pair. It acts as a nucleophile as it is electron loving.

Expert Solution
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Answer to Problem 2.67P

The product formed by the reaction of (CH3CH2)3C+ with H2O is (CH3CH2)3CO+H2.

Explanation of Solution

In the given reaction, Lewis base H2O reacts with Lewis acid (CH3CH2)3C+ . Electron pair present on the oxygen atom of Lewis base is donated to the carbon of Lewis acid. The product formed is shown below.

ORGANIC CHEMISTRY, Chapter 2, Problem 2.67P , additional homework tip  1

Figure 1

Conclusion

The product formed by the reaction of (CH3CH2)3C+ with H2O is (CH3CH2)3CO+H2.

Interpretation Introduction

(b)

Interpretation: The product formed by the reaction of Lewis acid (CH3CH2)3C+ with the given Lewis base is to be drawn.

Concept introduction: Lewis acid accepts an electron pair. It acts as an electrophile as it is electron deficient. Lewis base donates an electron pair. It acts as a nucleophile as it is electron loving.

Expert Solution
Check Mark

Answer to Problem 2.67P

The product formed by the reaction of (CH3CH2)3C+ with CH3O¨¨ H is (CH3CH2)3CO+HCH3.

Explanation of Solution

In the given reaction, Lewis base CH3O¨¨ H reacts with Lewis acid (CH3CH2)3C+ . Electron pair present on the oxygen atom of Lewis base is donated to the carbon of Lewis acid. The product formed is shown below.

ORGANIC CHEMISTRY, Chapter 2, Problem 2.67P , additional homework tip  2

Figure 2

Conclusion

The product formed by the reaction of (CH3CH2)3C+ with CH3O¨¨ H is (CH3CH2)3CO+HCH3.

Interpretation Introduction

(c)

Interpretation: The product formed by the reaction of Lewis acid (CH3CH2)3C+ with the given Lewis base is to be drawn.

Concept introduction: Lewis acid accepts an electron pair. It acts as an electrophile as it is electron deficient. Lewis base donates an electron pair. It acts as a nucleophile as it is electron loving.

Expert Solution
Check Mark

Answer to Problem 2.67P

The product formed by the reaction of (CH3CH2)3C+ with CH3O¨¨CH3 is (CH3CH2)3CO+(CH3)2.

Explanation of Solution

In the given reaction, Lewis base CH3O¨¨CH3 reacts with Lewis acid (CH3CH2)3C+ .Electron pairs present on the oxygen atom of Lewis base is donated to the carbon of Lewis acid. The product formed is shown below.

ORGANIC CHEMISTRY, Chapter 2, Problem 2.67P , additional homework tip  3

Figure 3

Conclusion

The product formed by the reaction of (CH3CH2)3C+ with CH3O¨¨CH3 is (CH3CH2)3CO+(CH3)2.

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Chapter 2 Solutions

ORGANIC CHEMISTRY

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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