Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 10.4, Problem 19P
What stereoisomers are formed in the following reactions? Which stereoisomer is the major product?
- a. the acid-catalyzed dehydration of 1-pentanol to 2-pentene
- b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexene
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--
14:33 A
Candidate Identification
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11. Compound A can transform into
compound B through an organic reaction.
From the structures below, mark the
correct one:
HO
A
تھے۔
די
HO
B
○ A) Compounds A and B are isomers.
B) Both have the same number of chiral
carbons.
C) Compound A underwent an addition
reaction of Cl2 and H2O to form
compound B.
D) Compound A underwent a
substitution reaction forming the
intermediate chlorohydrin to obtain
compound B.
E) Compound A underwent an addition
reaction of Cl2 forming the chloronium
ion and then added methanol to obtain
compound B.
60
--
14:40 A
Candidate Identification
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13. The compound 1-bromo-hex-2-ene
reacts with methanol to form two
products. About this reaction, mark the
correct statement:
OCH3
CH3OH
Br
OCH3 +
+ HBr
A
B
A) The two products formed will have
the same percentage of formation.
B) Product B will be formed by SN1
substitution reaction with the formation
of an allylic carbocation.
C) Product A will be formed by SN1
substitution reaction with the formation
of a more stable carbocation than
product B.
D) Product A will be formed by an SN2
substitution reaction occurring in two
stages, the first with slow kinetics and
the second with fast kinetics.
E) The two compounds were obtained
by addition reaction, with compound B
having the highest percentage of
formation.
57
--
☑
14:30 A
Candidate Identification
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10. Amoxicillin (figure X) is one of the
most widely used antibiotics in the
penicillin family. The discovery and
synthesis of these antibiotics in the 20th
century made the treatment of infections
that were previously fatal routine.
About amoxicillin, mark the correct one:
HO
NH2 H
S
-N.
HO
Figura X. Amoxicilina
A) It has the organic functions amide,
ester, phenol and amine.
B) It has four chiral carbons and 8
stereoisomers.
C) The substitution of the aromatic ring
is of the ortho-meta type.
D) If amoxicillin reacts with an alcohol it
can form an ester.
E) The structure has two tertiary
amides.
62
Chapter 10 Solutions
Organic Chemistry (8th Edition)
Ch. 10.1 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 10.1 - Explain the difference in reactivity between...Ch. 10.1 - Prob. 5PCh. 10.1 - Prob. 6PCh. 10.1 - Prob. 8PCh. 10.2 - Prob. 9PCh. 10.3 - Prob. 11PCh. 10.3 - Show how 1-propanol can be converted into the...Ch. 10.4 - Which of the following alcohols dehydrates the...Ch. 10.4 - Prob. 14P
Ch. 10.4 - Prob. 15PCh. 10.4 - Propose a mechanism for each of the following...Ch. 10.4 - Draw the product of each of the following...Ch. 10.4 - Explain why the following alcohols, when heated...Ch. 10.4 - What stereoisomers are formed in the following...Ch. 10.4 - Prob. 20PCh. 10.4 - What alcohol would you treat with phosphorus...Ch. 10.5 - Prob. 22PCh. 10.6 - What are the major products obtained when each of...Ch. 10.6 - Prob. 26PCh. 10.7 - Prob. 27PCh. 10.7 - Would you expect the reactivity of a five-membered...Ch. 10.7 - Prob. 29PCh. 10.7 - What products are obtained from the reaction of...Ch. 10.7 - Prob. 31PCh. 10.7 - Prob. 32PCh. 10.7 - Prob. 33PCh. 10.8 - Draw the mechanism for formation of the two...Ch. 10.8 - Prob. 35PCh. 10.8 - Prob. 36PCh. 10.8 - How do the major products obtained from...Ch. 10.8 - Explain why the two arene oxides in Problem 38...Ch. 10.8 - Which compound is more likely to be carcinogenic?Ch. 10.8 - Three arene oxides can be obtained from...Ch. 10.9 - Explain why the half-life (the time it takes for...Ch. 10.10 - Prob. 43PCh. 10.10 - Prob. 44PCh. 10.10 - Prob. 45PCh. 10.10 - Prob. 46PCh. 10.10 - Prob. 47PCh. 10.10 - Describe a synthesis for each of the following...Ch. 10.11 - Using an alkyl halide and a thiol as starting...Ch. 10.11 - The following three nitrogen mustards were studied...Ch. 10.11 - Why is melphalan a good cancer drug?Ch. 10.11 - Prob. 53PCh. 10.12 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 55PCh. 10 - Which compound is more likely to be carcinogenic?Ch. 10 - Prob. 57PCh. 10 - Prob. 58PCh. 10 - When heated with H2SO4, both...Ch. 10 - What is the major product obtained from the...Ch. 10 - Write the appropriate reagent over each arrow.Ch. 10 - What alkenes would you expect to be obtained from...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - When deuterated phenanthrene oxide undergoes a...Ch. 10 - An unknown alcohol with a molecular formula of...Ch. 10 - Explain why the acid-catalyzed dehydration of an...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - What product would be formed if the four-membered...Ch. 10 - Which of the following ethers would be obtained in...Ch. 10 - Using the given starting material any necessary...Ch. 10 - Prob. 74PCh. 10 - When 3-methyl-2-butanol is heated with...Ch. 10 - Draw structures for compounds AF.Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - How could you synthesize isopropyl propyl ether,...Ch. 10 - When ethyl ether is heated with excess HI for...Ch. 10 - When the following seven-membered ring alcohol is...Ch. 10 - Ethylene oxide reacts readily with HO because of...Ch. 10 - Describe how each of the following compounds could...Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - Triethylene glycol is one of the products obtained...Ch. 10 - Prob. 85PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 87PCh. 10 - An ion with a positively charged nitrogen atom in...Ch. 10 - The following reaction takes place several times...Ch. 10 - Prob. 90PCh. 10 - Propose a mechanism for each of the following...Ch. 10 - A vicinal diol has OH groups on adjacent carbons....Ch. 10 - Prob. 93PCh. 10 - Prob. 94PCh. 10 - Two stereoisomers are obtained from the reaction...Ch. 10 - Propose a mechanism for each or the following...Ch. 10 - Triethylenemelamine (TEM) is an antitumor agent....
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