1 Structure And Bonding 2 Acids And Bases 3 Introduction To Organic Molecules And Functional Groups 4 Alkanes 5 Stereochemistry 6 Understanding Organic Reactions 7 Alkyl Halides And Nucleophilic Substitution 8 Alkyl Halides And Elimination Reactions 9 Alcohols, Ethers, And Related Compounds 10 Alkenes 11 Alkynes 12 Oxidation And Reduction 13 Mass Spectrometry And Infrared Spectroscopy 14 Nuclear Magnetic Resonance Spectroscopy 15 Radical Reactions 16 Conjugation, Resonance, And Dienes 17 Benzene And Aromatic Compounds 18 Reactions Of Aromatic Compounds 19 Carboxylic Acids And The Acidity Of The O-h Bond 20 Introduction To Carbonyl Chemistry; Organometallic Reagents; Oxidation And Reduction 21 Aldehydes And Ketones-nucleophilic Addition 22 Carboxylic Acids And Their Derivatives-nucleophilic Acyl Substitution 23 Substitution Reactions Of Carbonyl Compounds At The α Carbon 24 Carbonyl Condensation Reactions 25 Amines 26 Carbon–carbon Bond-forming Reactions In Organic Synthesis 27 Pericyclic Reactions 28 Carbohydrates 29 Amino Acids And Proteins 30 Synthetic Polymers 31 Lipids expand_more
Chapter Questions expand_more
Problem 2.1P: a. Which compounds are Bronsted-Lowry acids: HBr,NH3,CCl4? b. Which compounds are Bronsted-Lowry... Problem 2.2P: a. Draw the conjugate acid of each base: NH3,Cl,(CH3)2C=O. b. Draw the conjugate base of each acid:... Problem 2.3P: Label each statement as True or False.
a. is the conjugate acid of.
b. is the conjugate base... Problem 2.4P: Label the acid and base, and the conjugate acid and base in the following reactions. Use curved... Problem 2.5P: Decide which compound is the acid and which is the base, and draw the products of each proton... Problem 2.6P: Draw the products formed from the acid-base reaction of HCl with each compound. a.b. c. d. Problem 2.7P: Which compound in each pair is the stronger acid? a. CH3CH2CH3 or CH3CH2OHb. or pKa=50pKa=16... Problem 2.8P: Use a calculator when necessary to answer the following questions. a.What is the pKa for each Ka:... Problem 2.9P: Rank the conjugate bases of each of group of acids in order of increasing basicity. a NH3,H2O, CH4.... Problem 2.10P: Problem-2.10 Considers two acids: (formic acid,) and pivalic acid
. (a) Which acid has the larger ?... Problem 2.11P Problem 2.12P: Draw the products of each reaction and determine the direction of equilibrium. a.c. b.d. Problem 2.13P Problem 2.14P: Without reference to a pKa table, decide which compound in each pair is the stronger acid. a. or b.... Problem 2.15P: Rank the labeled H atoms in the following compound in order of increasing acidity. Problem 2.16P: Which hydrogen in each molecule is most acidic?
a. b. c.
Problem 2.17P: Which hydrogen in pseudoephedrine, the nasal decongestant in the commercial medication Sudafed, is... Problem 2.18P: Which compound in each pair of isomers is the stronger acid? a. b. Problem 2.19P: Which compound in each pair is the stronger acid? a.orc. or b.or Problem 2.20P: Glycolic acid, HOCH2CO2H, is the simplest member of a group of compounds called - hydroxy acids... Problem 2.21P: Explain the apparent paradox. HBr is a stronger acid than HCl, but HOCl is a stronger acid than... Problem 2.22P: The CH bond in acetone, (CH3)2C=O, has a pKa of 19.2. Draw two resonance structures for its... Problem 2.23P: Acetonitrile (CH3CN) has a pKa of 25, making it more acidic than many other compounds having only... Problem 2.24P: For each pair of compounds: [1] Which indicated H is more acidic? [2] Draw the conjugate base of... Problem 2.25P: Rank the compounds in each group in order of increasing acidity. a. b. c. Problem 2.26P: Which proton in each of the following drugs is most acidic? THC is the active component in... Problem 2.27P: Which anion A or B is the stronger base? AB Problem 2.28P Problem 2.29P: Problem 2.29
Compounds like amphetamine that contain nitrogen atoms are protonated by the in the... Problem 2.30P: Problem 2.30 Which species are Lewis bases?
a. b. c. d.
Problem 2.31P: Which species are Lewis acids?
a. b. c. d.
Problem 2.32P: For each reaction, label the Lewis acid and base. Use curved arrow notation to show the movement of... Problem 2.33P Problem 2.34P Problem 2.35P: Label the Lewis acid and base. Use curved arrow notation to show the movement of electron pairs. Problem 2.36P: 2.36 Propranolol is an antihypertensive agent—that is, it lowers blood pressure. (a)
Which proton... Problem 2.37P: 2.37 Amphetamine is a powerful stimulant of the central nervous system. (a) Which
proton in... Problem 2.38P: 2.38 What is the conjugate acid of each base?
a. b. c. d.
Problem 2.39P: 2.39 What is the conjugate base of each acid?
a. b. c. d.
Problem 2.40P: 2.40 Draw the products formed from the acid-base reaction of H2SO4 with each
compound.
a. b. c.... Problem 2.41P: Draw the products formed from the acid-base reaction of KOH with each compound. a. b. c. d. Problem 2.42P: Draw the products of each proton transfer reaction. Label the acid and base in the starting... Problem 2.43P Problem 2.44P Problem 2.45P: What is Ka for each compound? Use a calculator when necessary. a. H2SpKa=7.0 b. ClCH2COOHpKa=2.8 c.... Problem 2.46P: What is the pKa for each compound? a. b. c. Problem 2.47P: Which of the following bases are strong enough to deprotonate CH3CH2CH2CCH(pKa=25), so that... Problem 2.48P: Which compounds can be deprotonated by OH, so that equilibrium favors the products? Refer to the pKa... Problem 2.49P: Draw the products of each reaction. Use the pKa table in Appendix A to decide if the equilibrium... Problem 2.50P: Rank the following compounds in order of increasing acidity. a.c. b.d. Problem 2.51P: 2.51 Rank the following ions in order of increasing basicity.
a. c.
b. d.
Problem 2.52P Problem 2.53P Problem 2.54P: 2.54 The of three bonds is given below.
a. For each compound, draw the conjugate base, including... Problem 2.55P: a. What is the conjugate acid of A? b. What is the conjugate base of A? Problem 2.56P: 2.56 Draw the structure of a constitutional isomer of compound that fits each
description.
An... Problem 2.57P: 2.57 Many drugs are Bronsted-Lowry acids or bases.
a. What is the most acidic proton in the... Problem 2.58P: Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH) are isomers, but has (CH3OCH3) a pKa of 40 and... Problem 2.59P: 2.59 Atenolol is a (beta) blocker, a drug used to treat high blood pressure. Which of
the... Problem 2.60P: 2.60 Use the principles in Section 2.5 to label the most acidic hydrogen in each drug.
Explain your... Problem 2.61P: 2.61 Label the three most acidic hydrogen atoms in lactic acid. and
rank them in order of deceasing... Problem 2.62P Problem 2.63P: 2.63 Classify each compound as a Lewis base, a Bronsted-Lowry base, both, or neither.
a. b. c. d.... Problem 2.64P: 2.64 Classify each species as a Lewis acid, a Bronsted-Lowry acid, both, or neither.
a. b. C. d.... Problem 2.65P: Label the Lewis acid and Lewis base in each reaction. Use curv ed arrows to show the movement of... Problem 2.66P: 2.66 Draw the products of each Lewis acid-base reaction. Label the electrophile and
nucleophile.
a.... Problem 2.67P Problem 2.68P: 2.68 Answer the following questions about the four species .
A B C ... Problem 2.69P Problem 2.70P: 2.70 Hydroxide can react as a Brønsted-Lowry base (and remove a proton), or a
Lewis base (and... Problem 2.71P: 2.71 Answer the following questions about esmolol, a drug used to treat high blood pressure sold... Problem 2.72P: 2.72 DBU, is a base we will encounter in elimination
reaction in chapter 8, Which N atom is more... Problem 2.73P: 2.73 Molecules like acetamide can be protonated on either their or atoms
when treated with a... Problem 2.74P Problem 2.75P Problem 2.76P: 2.76 Write a stepwise reaction sequence using proton transfer reactions to show how the
following... Problem 2.77P Problem 2.78P: 2.78 Which compound, M or N, is the stronger acid? Explain your choice.
M N
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