ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 3, Problem 3.64P
Explain why A is less water soluble than B, even though both compounds have the same
Expert Solution & Answer
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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
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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 3 Solutions
ORGANIC CHEMISTRY
Ch. 3 - Prob. 3.1PCh. 3 - (a) Classify the carbon atoms in each compound as...Ch. 3 - Problem 3.3 Classify a carbon atom by the number...Ch. 3 - Classify each alkyl halide and alcohol as , or...Ch. 3 - Prob. 3.5PCh. 3 - Prob. 3.6PCh. 3 - Draw the structure of a compound of molecular...Ch. 3 - Prob. 3.8PCh. 3 - Prob. 3.9PCh. 3 - Draw the structure of a compound fitting each...
Ch. 3 - Draw structures that fit each description and name...Ch. 3 - What types of intermolecular forces are present in...Ch. 3 - Which compound in each pair has the higher boiling...Ch. 3 - Explain why the boiling point of propanamide, is...Ch. 3 - Predict which compound in each pair has the higher...Ch. 3 - Prob. 3.16PCh. 3 - Which compounds are water soluble? a. b. c.Ch. 3 - a Label the hydrophobic and hydrophilic portions...Ch. 3 - Prob. 3.19PCh. 3 - Prob. 3.20PCh. 3 - Prob. 3.21PCh. 3 - Prob. 3.22PCh. 3 - Problem 3.23 (a) What types of intermolecular...Ch. 3 - Prob. 3.24PCh. 3 - Prob. 3.25PCh. 3 - Problem 3.26 Label the electrophilic and...Ch. 3 - Problem 3.27 Considering only electron density,...Ch. 3 - Prob. 3.28PCh. 3 - 3.29
Identify the functional groups in the...Ch. 3 - Prob. 3.30PCh. 3 - 3.31 For each alkane: (a) classify each carbon...Ch. 3 - 3.32 Identify the functional groups in each...Ch. 3 - 3.33 Identify each functional group located in the...Ch. 3 - 3.34 (a)Identify the functional groups in...Ch. 3 - Draw seven constitutional isomers with molecular...Ch. 3 - Prob. 3.36PCh. 3 - Prob. 3.37PCh. 3 - Prob. 3.38PCh. 3 - Intramolecular force of attraction are often...Ch. 3 - 3.40 (a) Draw four compounds with molecular...Ch. 3 - 3.41 Rank the compounds in each group in order of...Ch. 3 - Explain why CH3CH2NHCH3 has higher boiling point...Ch. 3 - Prob. 3.43PCh. 3 - 3.44 Rank the following compounds in order of...Ch. 3 - Prob. 3.45PCh. 3 - 3.46 Rank the following compounds in order of...Ch. 3 - 3.47 Which of the following molecules can hydrogen...Ch. 3 - 3.48 Explain why diethylether and have similar...Ch. 3 - Prob. 3.49PCh. 3 - 3.50 Predict the solubility of each of the...Ch. 3 - Prob. 3.51PCh. 3 - Prob. 3.52PCh. 3 - 3.53 THC is the active component in marijuana, and...Ch. 3 - Prob. 3.54PCh. 3 - Prob. 3.55PCh. 3 - 3.56 Label the electrophilic and nucleophilic...Ch. 3 - 3.57 By using only electron density arguments,...Ch. 3 - 3.58 The composition of a cell membrane is not...Ch. 3 - Prob. 3.59PCh. 3 - 3.60 Quinapril (trade name Accupril) is a drug...Ch. 3 - 3.61 Answer each question about oxycodone, a...Ch. 3 - Prob. 3.62PCh. 3 - Prob. 3.63PCh. 3 - 3.64 Explain why A is less water soluble than B,...Ch. 3 - 3.65 Recall from section 1.10B that there is...
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