ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Question
Chapter 2, Problem 2.62P
Interpretation Introduction
Interpretation: The more basic nitrogen in Bupivacaine is to be identified.
Concept introduction: Bupivacaine is an anesthetic that blocks the nerve impulses.
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Students have asked these similar questions
Bupivacaine (trade name Marcaine) is a quick-acting anesthetic often used during labor and delivery. Which nitrogen atom in bupivacaine is more basic? Explain your reasoning.
18.64 The following two
compounds each exhibit two
heteroatoms (one nitrogen
atom and one oxygen atom).
:0
Compound A
-N
Compound B
O
In compound A, the lone pair on the nitrogen atom is more
likely to function as a base. However, in compound B, the lone
pair on the oxygen atom is more likely to function as a base.
Explain this difference.
Explain why m-nitroaniline is a stronger base than p-nitroaniline.
Chapter 2 Solutions
ORGANIC CHEMISTRY
Ch. 2 - a. Which compounds are Bronsted-Lowry acids:...Ch. 2 - a. Draw the conjugate acid of each base:...Ch. 2 - Label each statement as True or False.
a. is the...Ch. 2 - Label the acid and base, and the conjugate acid...Ch. 2 - Decide which compound is the acid and which is the...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Which compound in each pair is the stronger acid?...Ch. 2 - Use a calculator when necessary to answer the...Ch. 2 - Rank the conjugate bases of each of group of acids...Ch. 2 - Problem-2.10 Considers two acids: (formic acid,)...
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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- Quinapril (trade name Accupril) is a drug used to treat hypertension andcongestive heart failure. (See in attached file) Question: Which site is most basic ?arrow_forwardHistamine, whose release in the body triggers nasal secretions and constricted airways, has three nitrogen atoms. List them in order of increasing basicity and explain your ordering.arrow_forwardGive clear detailed Solution with explanation needed..don't give Handwritten answerarrow_forward
- Be sure to answer all parts. Classify each nitrogen-containing functional group in the anesthetic lidocaine according to whether it is an amide, or a primary, secondary, or tertiary amine. dinh Functional group 1 is a(n) (select) Functional group 2 is a(n) (select) (select) amide 1° amine 2° amine 3° aminearrow_forwardQuinapril (trade name Accupril) is a drug used to treat hypertension andcongestive heart failure. (See in attached file) Question: Classify any alcohol, amide, or amine as 1°, 2°, or 3°.arrow_forwardWhy is the water solubility of a carboxylate salt greater than that of its parent carboxylic acid? A) A carboxylate salt is an ionic compound which is soluble in water. B) A carboxylate salt is less polar than its parent carboxylic acid. C) A carboxylate salt has a lower boiling point than its parent carboxylic acid. D) A carboxylate salt is more readily reduced to an aldehyde than its parent carboxylic acid.arrow_forward
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