Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 2, Problem 75P
Answer the following questions about esmolol, a drug used to treat high blood pressure sold under the trade name Brevibloc.
a. Label the most acidic hydrogen atom in esmolol.
b. What products are formed when esmolol is treated with
c. What products are formed when esmolol is treated with
d. Label all
e. Label the only triagonal pyramidal atom.
f. Label all C’s that bear
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Answer the following questions about esmolol, a drug used to treat high blood pressure sold under the trade name Brevibloc.a.Label the most acidic hydrogen atom in esmolol.
b.What products are formed when esmolol is treated with NaH?
c.What products are formed when esmolol is treated with HCl?
d. Label all sp2 hybridized C atoms.
e.Label the only trigonal pyramidal atom.
f.Label all C's that bear a δ+ charge.
What product is formed when each compound is treated with NaH? Each of these acid–base reactions was a step in a synthesis of a commercially available drug.
Draw the products of each acid-base reaction.
H CH3
H CH,CH,NHCH3
COOH
+
а.
NAOH
b.
CF3
+
HCI
CH,O
naproxen
anti-inflammatory agent
fluoxetine
antidepressant
1
1
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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- Rank the compounds in each group in order of increasing basicity.arrow_forwardDraw the structure of a constitutional isomer of compound B that fits each description. a. an isomer that is at least 105 times more acidic than B b. an isomer that is at least 10 times less acidic than B c. an isomer that is comparable in acidity to B HO. Barrow_forwardRank the attached ions in order of increasing basicity.arrow_forward
- Which of the following indicated a-hydrogens is most acidic? ဝ CH3CH₂CH CH3CH₂CCH₂CH₂CH3 CH3CH₂CCH₂COCH₂CH3 ပင်,H CCH₂ COCHICH A. CH3CH₂COCH₂CH3 D. B. C. ₂CCH₂C CH3CH₂CCH₂CH3 E.arrow_forwardWhich is a stronger acid? a. HCl or HBr b. CH3CH2CH2NH3 or CH3CH2CH2OH2 c. CH3CH2CH2OH or CH3CH2CH2SHarrow_forwardRank the labeled N atoms in the anticancer drug imatinib (trade name Gleevec) in order of increasing basicity. Imatinib, sold as a salt with methanesulfonic acid (CH3SO3H), is used for the treatment of chronic myeloid leukemia as well as certain gastrointestinal tumors.arrow_forward
- Which is the more stable base? a. Br− or I− b. CH3O− or CH3S− c. CH3CH2O− or CH3COO− d. H2C CH or HC C− e. FCH2CH2COO− or CH2CH2COO- f. CLCH2CH2O- or CL2CHCH2O-arrow_forwardThe boiling points of a range of organic compounds (A-D) of similar Mol. Wt.s are given below. OH OMe A в D b.p. 46-50°C Explain why the boiling point of C is higher than that of D. Explain why the boiling point of B is higher than that of A. Explain why the boiling point of C is higher than that of A. Which of these four compounds is most acidic? What makes it so acidic? b.p. 78'C b.p. 141'C b.p. 79'C (i) (ii) (iii) (iv)arrow_forwardWhich is a stronger base? a. CH3O− or CH3S− b. H2O or HO− c. H2O or NH3 d. CH3CO− or CH3O−arrow_forward
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