Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Textbook Question
Chapter 2, Problem 46P
What is the
a.
b.
c.
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Draw the products of the reaction shown below. Use wedge and dash bonds
to indicate stereochemistry. Ignore inorganic byproducts.
OSO4 (cat)
(CH3)3COOH
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Calculate the reaction rate for selenious acid, H2SeO3, if 0.1150 M I-1 decreases to 0.0770 M in 12.0 minutes.
H2SeO3(aq) + 6I-1(aq) + 4H+1(aq) ⟶ Se(s) + 2I3-1(aq) + 3H2O(l)
Problem 5-31
Which of the following objects are chiral?
(a) A basketball
(d) A golf club
(b) A fork
(c) A wine glass
(e) A spiral staircase
(f) A snowflake
Problem 5-32
Which of the following compounds are chiral? Draw them, and label the chirality centers.
(a) 2,4-Dimethylheptane
(b) 5-Ethyl-3,3-dimethylheptane
(c) cis-1,4-Dichlorocyclohexane
Problem 5-33
Draw chiral molecules that meet the following descriptions:
(a) A chloroalkane, C5H11Cl
(c) An alkene, C6H12
(b) An alcohol, C6H140
(d) An alkane, C8H18
Problem 5-36
Erythronolide B is the biological precursor of
erythromycin, a broad-spectrum antibiotic. How
H3C
CH3
many chirality centers does erythronolide B have?
OH
Identify them.
H3C
-CH3
OH
Erythronolide B
H3C.
H3C.
OH
OH
CH3
Chapter 2 Solutions
Organic Chemistry (6th Edition)
Ch. 2.1 - a. Which compounds are Bronsted-Lowry acids:...Ch. 2.2 - a. Draw the conjugate acid of each base:...Ch. 2.2 - Label each statement as True or False.
a. is the...Ch. 2.2 - Decide which compound is the acid and which is the...Ch. 2.2 - Draw the products formed from the acid-base...Ch. 2.3 - Which compound in each pair is the stronger acid?...Ch. 2.3 - Use a calculator when necessary to answer the...Ch. 2.3 - Rank the conjugate bases of each of group of acids...Ch. 2.3 - Problem-2.10 Considers two acids: (formic acid,)...Ch. 2.3 - Prob. 11P
Ch. 2.4 - Draw the products of each reaction and determine...Ch. 2.4 - Prob. 13PCh. 2.5 - Without reference to a pKa table, decide which...Ch. 2.5 - Rank the labeled H atoms in the following compound...Ch. 2.5 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2.5 - Which compound in each pair is the stronger acid?...Ch. 2.5 - Glycolic acid, HOCH2CO2H, is the simplest member...Ch. 2.5 - Explain the apparent paradox. HBr is a stronger...Ch. 2.5 - The CH bond in acetone, (CH3)2C=O, has a pKa of...Ch. 2.5 - Prob. 23PCh. 2.5 - For each pair of compounds: [1] Which indicated H...Ch. 2.5 - Rank the compounds in each group in order of...Ch. 2.5 - Prob. 26PCh. 2.5 - Prob. 27PCh. 2.6 - Prob. 28PCh. 2.7 - Problem 2.29
Compounds like amphetamine that...Ch. 2.8 - Problem 2.30 Which species are Lewis bases?
a. b....Ch. 2.8 - Which species are Lewis acids?
a. b. c. d.
Ch. 2.8 - For each reaction, label the Lewis acid and base....Ch. 2.8 - Prob. 33PCh. 2.8 - Prob. 34PCh. 2.8 - 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 - Draw the products of each proton transfer...Ch. 2 - Prob. 43PCh. 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 - Draw the products of each reaction. Use the pKa...Ch. 2 - a. What is the conjugate acid of A? b. What is the...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. 66PCh. 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. 71PCh. 2 - 2.68 Answer the following questions about the four...Ch. 2 - Prob. 73PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - Prob. 76PCh. 2 - Prob. 77PCh. 2 - Prob. 82P
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- Problem 5-48 Assign R or S configurations to the chirality centers in ascorbic acid (vitamin C). OH H OH HO CH2OH Ascorbic acid O H Problem 5-49 Assign R or S stereochemistry to the chirality centers in the following Newman projections: H Cl H CH3 H3C. OH H3C (a) H H H3C (b) CH3 H Problem 5-52 Draw the meso form of each of the following molecules, and indicate the plane of symmetry in each: OH OH (a) CH3CHCH2CH2CHCH3 CH3 H3C. -OH (c) H3C CH3 (b) Problem 5-66 Assign R or S configurations to the chiral centers in cephalexin, trade-named Keflex, the most widely prescribed antibiotic in the United States. H2N H IHH S Cephalexin N. CH3 CO₂Harrow_forwardSteps and explanationn please.arrow_forwardSteps and explanationn please.arrow_forward
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