Day 2 quiz questions
• Explain the differences between hyperconjugation,
resonance, and induction.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
11 -1
Day 2 quiz questions
• Show all significant resonance contributors and a
resonance hybrid for the following molecule.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
11 -2
Day 2 quiz questions
• Explain what is
incorrect about
each of the
mechanistic
steps shown
below.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
11 -3
Day 2 quiz questions
• Give the major product(s) for the reaction below.
Carefully consider regiochemistry and stereochemistry.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
11 -4
Day 2 quiz questions
• Predict the major product for the reaction below and
explain why NBS is preferred over Br2.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
11 -5
Day 3 quiz questions
• Draw the monomer necessary to synthesize the given
polymer using a free radical mechanism.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
11 -6
Day 3 quiz questions
•
Give necessary reagents for the transformation below.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
12 -7
Day 4 quiz questions
•
Give necessary reagents for the transformation below.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
12 -8
Day 4 quiz questions
•
Name the following molecule
•
Draw (1R,2R)-1-(3,3-dimethylbutyl)-3,5-cyclohexadien1,2-diol
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
13 -9
Day 5 quiz questions
•
Use ARIO and solvation to rank the following molecules
in order of increasing pKa
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
13 -10
Day 5 quiz questions
•
Predict the products for the following processes
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
13 -11
Day 6 quiz questions
•
Design a synthesis for the following molecule starting
from an alkyl halide and a carbonyl, each having 5
carbons or less
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
13 -12
Day 6 quiz questions
•
Give necessary reagents for the multi-step synthesis
below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
13 -13
Day 7 quiz questions
• Name the following molecule
• Draw the structure for (4-methylcyclohexyl)phenylether
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
14 -14
Day 7 quiz questions
• Fill in the missing intermediates and reagents in the
scheme below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
14 -15
Day 8 quiz questions
• Fill in the missing intermediates and reagents in the
scheme below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
14 -16
Day 9 quiz questions
• Give necessary reagents to complete the synthesis
below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
14 -17
Day 10 quiz questions
• Explain the relationship between heat of hydrogenation
and stability of a pi system.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
17-18
Day 10 quiz questions
• Explain why the instability of electrons in a pi MO
directly relates to the number of nodes the orbital
posses.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
17-19
Day 10 quiz questions
• Give a complete mechanism and predict the major
product for the addition reaction below.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
17-20
Day 11 quiz questions
• Predict the products and give necessary conditions for
the compound below to undergo a retro Diels-Alder
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
17-21
Day 11 quiz questions
• Predict the products for the electrocyclic ring-opening
below with proper stereochemical configuration.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
17-22
Day 12 quiz questions
•
Give the names for the structures below.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
18-23
Day 12 quiz questions
•
Explain how we know that aromaticity is stabilizing
experimentally and how MO theory rationalizes that
stabilization.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
18-24
Day 13 quiz questions
•
Label each molecule below as aromatic, antiaromatic,
or nonaromatic
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
18-25
Day 13 quiz questions
•
Predict the major product(s) for the reaction below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
18-26
Day 13 quiz questions
•
•
•
Given NMR data, predict the structure of an aromatic
compound
1H NMR: a) triplet at 1.1 ppm integrates to 3
b) singlet at 2.0 integrates to 3
c) quartet at 2.3 integrates to 2
d) overlapping signals between 7-7.5
ppm
integrating to 8
13C NMR: signals at 12, 23, and 26 ppm and 8 signals
between 100 and 150 ppm
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
18-27
Day 15 quiz questions
• Give the products for the reaction below and a
complete mechanism
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
19-28
Day 16 quiz questions
• Predict the major product for each reaction below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
19-29
Day 16 quiz questions
• Give necessary reagents for the synthesis below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
19-30
Day 17 quiz questions
•
Fill in the blanks below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
18-31
Day 17 quiz questions
•
Give a reasonable name for the molecule below.
Copyright 2012 John Wiley &
Sons, Inc.
20 -32
Klein, Organic Chemistry 1e
Day 17 quiz questions
•
Give necessary reagents to make the carbonyl below
from an alkyne and also from an alkyl halide without
altering the number of carbons
Copyright 2012 John Wiley &
Sons, Inc.
20 -33
Klein, Organic Chemistry 1e
Day 18 quiz questions
•
Predict the major product and give a complete
mechanism.
Copyright 2012 John Wiley &
Sons, Inc.
20 -34
Klein, Organic Chemistry 1e
Day 18 quiz questions
•
Predict the structure of the enamine product in the
reaction below and show the last step of the
mechanism.
Copyright 2012 John Wiley &
Sons, Inc.
20 -35
Klein, Organic Chemistry 1e
Day 19 quiz questions
•
Give necessary Wittig reagents and conditions to
synthesize the molecule below and show a complete
mechanism.
Copyright 2012 John Wiley &
Sons, Inc.
20 -36
Klein, Organic Chemistry 1e
Day 19 quiz questions
•
Give reagents necessary for the synthesis below
Copyright 2012 John Wiley &
Sons, Inc.
20 -37
Klein, Organic Chemistry 1e
Day 19 quiz questions
• Give an appropriate name for the compound below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
21-38
Day 19 quiz questions
• Rank the following molecules by increasing pKa values.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
21-39
Day 19 quiz questions
• Predict the products for the reactions below.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
21-40
Day 20 quiz questions
• Using induction, sterics, and resonance, explain why
acid halides are especially electrophilic from a kinetic
persepective.
• Using the quality of the leaving group, explain why acid
halides are especially reactive from a thermodynamic
perspective.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
21-41
Day 22 quiz questions
• Give reagents necessary for the synthesis below where
all carbon atoms in the product come from a molecule
of the reactant
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
21-42
Day 23 quiz questions
• Explain why an enolate is more likely to produce
products resulting from attack by the alpha carbon
than direct attack by the oxygen. Is the argument
kinetic or thermodynamic or both?
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
22-43
Day 24 quiz questions
• Give the major products for the reaction below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
22-44
Day 24 quiz questions
• Using both kinetic and thermodynamic arguments,
explain why aldol reactions involving a ketone are less
product favored than those involving aldehydes
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
22-45
Day 24 quiz questions
• Give reagents necessary to produce the product below
using aldol chemistry.
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
22-46
Day 25 quiz questions
• Give reagents necessary for the synthesis below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
22-47
Day 25 quiz questions
• Give reagents necessary for the synthesis below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
22-48
Day 26 quiz questions
• Give an appropriate name for the following molecule
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
23-75
Day 26 quiz questions
• Predict the major product for the following reaction
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
23-750
Day 27 quiz questions
• Give necessary reagents to make the secondary amine
below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
23-517
Day 27 quiz questions
• Give necessary reagents for the synthesis below
Copyright 2012 John Wiley &
Sons, Inc.
Klein, Organic Chemistry 1e
23-78