ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Chapter 18, Problem 18.71SP
The UV spectrum of an unknown compound shows values of λmax at 225 nm (ε=10,000) and at 318 nm (ε=40). The mass spectrum shows a molecular ion at m/z 96 and a prominent base peak at m/z 68 The IR and NMR spectra follow. Propose a structure, and show how your structure corresponds to the observed absorptions. Propose a favorable fragmentation to account for the MS base peak at m/z 68 (loss of C2H4).
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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 18 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
Ch. 18.3 - Give the IUPAC name and (if possible) a common...Ch. 18.5D - NMR spectra for two compounds are given here,...Ch. 18.5D - Why were no products from the McLafferty...Ch. 18.5D - Use equations to show the fragmentation leading to...Ch. 18.5E - Prob. 18.5PCh. 18.7D - Show how you would synthesize each compound from...Ch. 18.8 - Prob. 18.7PCh. 18.9 - Predict the products of the following reactions....Ch. 18.9 - Show how the following transformations may be...Ch. 18.10 - Prob. 18.10P
Ch. 18.11 - Show how you would accomplish the following...Ch. 18.11 - Prob. 18.12PCh. 18.12 - Propose mechanisms for a. the acid-catalyzed...Ch. 18.12 - Rank the following compounds in order of...Ch. 18.13 - Prob. 18.15PCh. 18.13 - Show how you would accomplish the following...Ch. 18.14 - Prob. 18.17PCh. 18.14 - Prob. 18.18PCh. 18.14 - Prob. 18.19PCh. 18.14 - Prob. 18.20PCh. 18.15 - 2,4-Dinitrophenylhydrazine is frequently used for...Ch. 18.15 - Prob. 18.22PCh. 18.15 - Prob. 18.23PCh. 18.16 - Prob. 18.24PCh. 18.16 - Prob. 18.25PCh. 18.16 - Show what alcohols and carbonyl compounds give the...Ch. 18.16 - In the mechanism for acetal hydrolysis shown, the...Ch. 18.16 - Prob. 18.28PCh. 18.17 - Show how you would accomplish the following...Ch. 18.18 - Prob. 18.30PCh. 18.18 - Prob. 18.31PCh. 18.18 - Prob. 18.32PCh. 18.18 - Show how Wittig reactions might be used to...Ch. 18.19 - Predict the major products of the following...Ch. 18.20C - Prob. 18.35PCh. 18.20C - Predict the major products of the following...Ch. 18 - Draw structures of the following derivatives. a....Ch. 18 - Prob. 18.38SPCh. 18 - Predict the major products of the following...Ch. 18 - Rank the following carbonyl compounds in order of...Ch. 18 - Acetals can serve as protecting groups for...Ch. 18 - Sketch the expected proton NMR spectrum of...Ch. 18 - A compound of formula C6H10O2 shows only two...Ch. 18 - The proton NMR spectrum of a compound of formula...Ch. 18 - The following compounds undergo McLafferty...Ch. 18 - An unknown compound gives a molecular ion of m/z...Ch. 18 - Show how you would accomplish the following...Ch. 18 - Prob. 18.48SPCh. 18 - Prob. 18.49SPCh. 18 - Propose mechanisms for the following reactions.Ch. 18 - Show how you would accomplish the following...Ch. 18 - Show how you would synthesize the following...Ch. 18 - Predict the products formed when cyclohexanone...Ch. 18 - Predict the products formed when...Ch. 18 - Show how you would synthesize octan-2-one from...Ch. 18 - Prob. 18.56SPCh. 18 - Both NaBH4 and NaBD4 are commercially available,...Ch. 18 - When LiAIH4 reduces 3-methylcyclopentanone, the...Ch. 18 - Prob. 18.59SPCh. 18 - Show how you would accomplish the following...Ch. 18 - There are three dioxane isomers 1,2-dioxane,...Ch. 18 - Two structures for the sugar glucose are shown on...Ch. 18 - Prob. 18.63SPCh. 18 - Prob. 18.64SPCh. 18 - Prob. 18.65SPCh. 18 - Prob. 18.66SPCh. 18 - Within each set of structures, indicate which will...Ch. 18 - Prob. 18.68SPCh. 18 - Prob. 18.69SPCh. 18 - Prob. 18.70SPCh. 18 - The UV spectrum of an unknown compound shows...Ch. 18 - a. Simple aminoacetals hydrolyze quickly and...Ch. 18 - The mass spectrum of unknown compound A shows a...Ch. 18 - Prob. 18.74SPCh. 18 - Prob. 18.75SPCh. 18 - Prob. 18.76SPCh. 18 - Prob. 18.77SP
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