TODAY 0503

1
TODAY (05/03)
Quiz Review Enolates ( the quantitative case,
aceto/malonic) Enolates ( catalytic case,
claisen/aldol) The Michael Rxn Example Problem
Problems 23.41, 23.44, 23.45, 24.1, and
24.48 AMCAM ( acetoacetic, malonic, claisen,
aldol michael)
2
TODAY (05/02)
Quiz Review Enolates ( the quantitative case,
aceto/malonic) Enolates ( catalytic case,
claisen/aldol) Rxn of enolate donors and
Michael acceptors
Problems 23.41, 23.44, 24.1, and 24.48 AMCAM
( acetoacetic, malonic, claisen, aldol michael)
3
TODAY (04/29)
Predicting Products Problems Solution for a
Spectroscopy Problem Enolates ( the quantitative
case, aceto/malonic) Enolates ( catalytic case,
aldol and claisen)
Reading Assignment Sections 23.11, 23.12, 23.14,
24.1, 24.4, and 24.9 Problems 22.24, 22.46 (b)
and 23.40 QUIZ V on Monday AMCAM (
acetoacetic, malonic, claisen, aldol michael)
4
TODAY (04/28)
Predicting Products Problems Solution for a
Spectroscopy Problem Enolate Chemistry and
Malonic Ester Synthesis
Reading Assignment Sections 23.11, 23.12, 23.14,
24.1, 24.4, and 24.9 Problems, 22.21 and 22.23
AMCAM ( acetoacetic, malonic, claisen, aldol
michael)
5
TODAY (05/03)
Enolate Chemistry and Malonic Ester Synthesis
Reading Assignment Sections 23.11, 23.12, 23.14,
24.1, 24.4, and 24.9 Problems, 22.21 and 22.23
AMCAM ( acetoacetic, malonic, claisen, aldol
michael)
6
TODAY (04/27)
Saponification Mechanism Reactivity of
Carboxylic Acid Derivatives( thioesters Acetyl
CoA) Synthetic Polymers (less reactive esters and
amides) Predicting Products Problems Solution
for a Spectroscopy Problem
Reading Assignment Sections 23.1 thru
23.3 Problems 22.21 and 22.23 AMCAM (
acetoacetic, malonic, claisen, aldol michael)
7
TODAY (04/26)
Thioesters and Acetyl Coenzyme A Fischer
Esterification Mechanism Saponification
Mechanism Synthetic Polymers (less reactive
esters and amides) Predicting Products Problems
Solution for a Spectroscopy Problem Malonic
Ester Synthesis Alpha-substitution and Enolates
Reading Assignment Sections 27.2, 27.3 and
23.1-23.3 Problems, (complete 4/21 problems)
AMCAM ( acetoacetic, malonic, claisen, aldol
michael)
8
TODAY (04/21)
Exam Review Reactivity of RCO2H
Derivatives Fischer Esterification of RCO2H and
NAcS Saponification Thioesters and Coenzyme A
Reading Assignment Sections 22.1-22.8really
focus on sections 22.5 and 22.8 Problems,
21.36, 21.37, 21.46, and 21.54 AMCAM (
acetoacetic, malonic, claisen, aldol michael)
9
TODAY (04/25)
Fischer Esterification and NAcS Reactivity of
RCO2H Derivatives Saponification Thioesters and
Coenzyme A
Reading Assignment Sections 27.2 and 27.3
Problems (complete 4/22 problems) AMCAM (
acetoacetic, malonic, claisen, aldol michael)
10
TODAY (04/22)
Exam Review Fischer Esterification and
NAcS Reactivity of RCO2H Derivatives
Saponification Thioesters and Coenzyme A
Reading Assignment Sections 22.1-22.8really
focus on sections 22.5 and 22.8 Problems,
21.36, 21.37, 21.46, and 21.54 AMCAM (
acetoacetic, malonic, claisen, aldol michael)
11
TODAY (04/18)
Fischer Esterification and NAcS Reactivity of
RCO2H Derivatives Exam Review Questions
Exam II April 20th and 22nd ( Chapters 17 thru
20 )
12
TODAY (04/15)
RCO2H by Carboxylation and Hydrolysis of
RCN Deprotonation and Esterification of
RCO2H Reduction of RCN to Amines
Problems 20.47 ,20.49, and 20.55 Exam II
April 20th and 22nd ( Chapters 17 thru 20 )
13
TODAY (04/14)
Direct vs Conjugate Addition Inductive Effects
and RCO2H Acidity Carboxylation Reduction and
Hydrolysis of Nitriles
Reading Assignment Sections 21.1-21.3, 21.6 and
21.8 Problems 21.36, 21.37, 21.46, and
21.54 Exam II April 19th ( Chapters 17 thru
20 )
14
TODAY (04/13)
Exptl Evidence for Acidity of RCO2H Inductive
Effects and RCO2H Chemistry Carboxylation Reducti
on and Hydrolysis of Nitriles
Problems 20.40 and 20.42 Exam II April
20th and 22nd ( Chapters 17 thru 20 )
15
TODAY (04/12)
Reactivity of RCHO versus R2CO Mechanism for
hydration and cyanohydrin formation Canizzarro
Rxn Direct vs Conjugate Addition
Reading Assignment Sections 20.5-20.10
Problems, 20.29 and 20.30 Exam II April
19th ( Chapters 17 thru 20 )
16
TODAY (04/11)
Canizzarro Rxn Direct vs Conjugate
Addition Exptl Evidence for Acidity of
RCO2H Inductive Effects and RCO2H Chemistry
Reading Assignment Section 20.10 and
21.1-21.4 Problems 20.29 and 20.30 Exam II
April 20th and 22nd ( Chapters 17 thru 20 )
17
TODAY (04/08)
Review of Class Assignment Canizzarro Rxn Direct
vs Conjugate Addition
Reading Assignment Section 20.9 Problems
19.16 and 19.17 Exam II April 20th and 22nd
( Chapters 17 thru 20 )
18
TODAY (04/07)
Neutral Nucleophiles Review of Class
Assignment The Wittig Reaction Example Problem
with the Wittig Rxn ( Tues Sections 19.5 thru
19.7, and 19.13.19.14) reactivity, hydration,
cyanohydrin, Cannizzaro, and direct vs conjugate
addition) )
Reading Assignment Sections 20.1-20.4
Problems, 19.16, 19.17 , 19.32 ( a, b, d, f,
g) , and 19.57 Exam II April 19th ( Chapters
17 thru 20 )
19
TODAY (04/05)
RSH, RSR, , R3S, RSSR, RS(O)R,
RSO2R Preparation of RCHO and R2CO (PCC, DIBAH,
ozone, Gilman) Tollens Reagent Nucleophilic
Addition
Reading Assignment Sections 19.9-19.14
Problems19.6, 19.40(a), 19.41 and 19.48 Class
Assignment Due Today Exam II April 19th (
Chapters 17 thru 20 )
20
TODAY (04/06)
Mechanism for hydration and cyanohydrin
formation The Wittig Reaction Review of Class
Assignment
Reading Assignment Sections 20.5-20.8 Problems
19.32 ( a, b, d, f, g) and 19.57 Exam II
April 20th and 22nd ( Chapters 17 thru 20 )
21
TODAY (04/04)
Reactivity of RCHO versus R2CO Mechanism for
hydration and cyanohydrin formation The Wittig
Reaction
Reading Assignment Sections 20.1-20.4 Problems
19.40(a) and 19.48 Class Assignment Due Today
22
TODAY (03/30)
Preparation of RCHO and R2CO (PCC, DIBAH, ozone,
Gilman) Tollens Reagent Nucleophilic Addition
Reactivity of RCHO versus R2CO
Reading Assignment Sections 19.9-19.14 Problems
Complete the class assignment, 19.6 and 19.41
23
TODAY (03/29)
Quiz Highlights Crown Ethers RSH, RSR, , R3S,
RSSR, RS(O)R, RSO2R Problems on NA PCC and
DIBAH
Reading Assignment Sections 19.1-19.8 Problems
19.4c, 19.30
24
TODAY (03/28)
RSH, RSR, , R3S, RSSR, RS(O)R,
RSO2R Problems on NA PCC and DIBAH Tollens
Reagent Nucleophilic Addition
Reading Assignment Sections 19.1-19.8 Problems
19.4c, 19.30
25
TODAY (03/25)
Quiz Highlights RSH, RSR, , R3S, RSSR,
RS(O)R, RSO2R
Reading Assignment pp 672-680 Problems
18.31,18.57, and 1-3 on pp 680-681
26
TODAY (03/24)
Preparation of ROR (Williamson Ether Synthesis
and Alkoxymercuration-Demercuration) Epoxides (
reactivity, acid and base catalyzed
rxns) Claisen rearrangement Crown Ethers
Reading Assignment pp 672-680 Problems 18.32,
18.40, 18.43, and 1-3 on pp 680-681 Quiz IV on
Tuesday
27
TODAY (03/23)
Epoxides ( base catalyzed rxns) Claisen
rearrangement Crown Ethers RSH, RSR, , R3S,
RSSR, RS(O)R, RSO2R
Problems 18.32 Quiz IV on Friday
28
TODAY (03/21)
Preparation of ROR (Williamson Ether Synthesis
and Alkoxymercuration-Demercuration) Epoxides (
reactivity, acid and base catalyzed rxns) Crown
Ethers
Problems 18.40 and 18.43
29
TODAY (03/24)
Preparation of ROR (Williamson Ether Synthesis
and Alkoxymercuration-Demercuration) Epoxides (
reactivity, acid and base catalyzed rxns) Crown
Ethers
Reading Assignment Sections 18.9
-18.11 Problems 18.22, 18.25(b,d,e, h) and
18.52
30
TODAY (03/22)
Chemistry of Phenols ( prep/rxns) Spectroscopy
of ROH/PhOH Naming ethers and properties Prepara
tion of ROR (Williamson Ether Synthesis and
Alkoxymercuration-Demercuration)
Reading Assignment Sections 18.9
-18.11 Problems 18.22, 18.25(b,d,e, h) and
18.52
31
TODAY (03/17)
Chemistry of Alcohols (preparation, protecting
groups) Chemistry of Phenols ( prep/rxns)
Spectroscopy of ROH/PhOH
Reading Assignment Sections 18.1 thru
18.8 Problems 17.25 , 17.41, 17.42, 17.44,
17.46, 17.48, and 17.52 a c
32
TODAY (03/18)
Naming ethers and properties Preparation of ROR
(Williamson Ether Synthesis and
Alkoxymercuration-Demercuration) Crown Ethers
Reading Sections18.9 -18.11 Problems 18.22,
18.25(b,d,e, h) and 18.52
33
TODAY (03/16)
Chemistry of Phenols ( prep/rxns) Spectroscopy
of ROH/PhOH Ethers, thiols, and sulfides
Problems 17.46, 17.48, and 17.52 a c
Reading 18.4-18.8
34
TODAY (03/15)
Chemistry of Alcohols (key general
characteristics, pKa, and rxns )
Reading Assignment Sections 17.9 thru
17.12 Problems 17.15, 17.36 and 17.57
35
TODAY (03/03
Benzylic Bromination Ring Reduction Chemistry
of Alcohols (key characteristics and pKa)
Reading Assignment pp 578-586 and Sections
17.1-17.8 Problems 3 and 4 on page 586 , 17.6,
17.7 , 17.8 and 17.26 (a, b, f) QuIz III Due
Today
36
TODAY (03/14)
Chemistry of Alcohols (preparation, protecting
groups) Chemistry of Phenols ( pKa)
Problems 17.25 , 17.41, 17.42, and 17.44
Reading 18.1-18.3
37
TODAY (03/04
Chemistry of Alcohols (preparation, protecting
groups)
Problems 17.36 QuIz III Due Today Reading
17.7-17.12
38
TODAY (03/02
Chemistry of Alcohols (pKa, preparation, rxns)
Problems 17.15 and 17.57 QuIz III Due on
Friday
39
TODAY (02/28)
Benzylic Bromination Ring Reduction Chemistry
of Alcohols
Problems 17.6, 17.7 , 17.8 and 17.26 (a, b, f)

40
TODAY (02/25)
Exam Highlights Benzylic Bromination Ring
Reduction
Problems 3 and 4 on page 586 Reading pp
578-586 and Sections 17.1-17.6
41
TODAY (02/22)
Acylation as an Alternative to Alkylation
(Clemmensen and Wolff-Kishner) Oxidation of
Alkylbenzenes NAS ( the reaction and
mechanism)
Problems 16.50, 16.51, 16.53, and 16.73 EXAM I
Thurs, 2/24( Chapters 12-16)
42
TODAY (02/22)
Acylation as an Alternative to Alkylation
(Clemmensen and Wolff-Kishner) Oxidation of
Alkylbenzenes NAS ( the reaction and
mechanism)
Problems 16.50, 16.51, 16.53, and 16.73 EXAM I
Thurs, 2/24( Chapters 12-16)
43
TODAY (02/21)
Acylation as an Alternative to Alkylation
(Clemmensen and Wolff-Kishner) Oxidation of
Alkylbenzenes NAS ( the reaction and
mechanism)
Problems 16.51 EXAM I Wed and Fri ..
2/23 and 2/25 ( Chapters 12-16)
44
TODAY (02/18)
Electrophilic Aromatic Substitution(EAS) (directin
g effects of ring substituents, reactivity
effects of ring substituentsinductive versus
resonance arguments) )
Problems 16.50, 16.53, and 16.73 EXAM I
Wed and Fri .. 2/23 and 2/25 ( Chapters 12-16)
45
TODAY (02/17)
Electrophilic Aromatic Substitution(EAS) (mechanis
m, energy profile, kinetics and directing effects
of ring substituents)
Problems 16.7 16.8 and 16.19 EXAM I
Thurs, 2/24( Chapters 12-16)
46
TODAY (02/16)
Electrophilic Aromatic Substitution(EAS) (mechanis
m, energy profile, kinetics and directing effects
of ring substituents)
Problems 16.7 16.8 and 16.19 EXAM I Wed
and Fri .. 2/23 and 2/25 ( Chapters 12-16)
47
TODAY (02/15)
Huckels 4n 2 ? Spectroscopy of Aromatic
Compounds Electrophilic Aromatic
Substitution(EAS)
Reading for this week Sections 16.1 16.8 and
16.10-16.11 Problems 16.29
48
TODAY (02/14)
Huckels 4n 2 ? Spectroscopy of Aromatic
Compounds Electrophilic Aromatic
Substitution(EAS)
Reading Sections 16.8, 16.10-16.11 Problems
16.29
49
TODAY (02/11)
Benzene Stability Huckels 4n 2 ? Rule and
the Case for Aromaticity
Reading Sections 16.1 16.6 for Mon and Wed
Problems 15.38, 15.47, and 16.36
50
TODAY (02/10)
Quiz II Highlights Case for Aromaticity
Problems 15.4, 15.9 15.19
51
TODAY (02/09)
Quiz II Highlights Benzene Stability Case for
Aromaticity
Problems 15.9 and 15.47
52
TODAY (02/08)
Naming Benzene Derivatives Benzene Stability Case
for Aromaticity
Problems 15.4, 15.9 15.19
53
TODAY (02/08)

• QUIZ II
• Estimate NMR (C-13 and proton) spectra for
  simple molecules like ethanal
• Propose a structure when given NMR spectra for a
  simple molecule like diethyl ether
• Discuss differences between proton and C-13 NMR
• Explain the basis of the chemical shift,
  integration, and the splitting patterns in NMR

54
TODAY (02/07)
Naming Benzene Derivatives Benzene Stability Case
for Aromaticity
Problems 15.4 15.19
55
TODAY (02/04)
NMR Spectroscopy C-13 (C-13 NMR) Naming
Benzene Derivatives
Problems 13.36 and 15.1 thru 15.3
56
TODAY (02/03e)
NMR Spectroscopy (C-13 NMR) Naming Benzene
Derivatives
Problems 15.1 thru 15.3
57
TODAY (02/01e)

• NMR (Principle and Application)
• (chemical shift, splitting patterns )

Reading Assignment for Chapter 15 Sections 15.1
thru 15.10 with emphasis on 15.2, 15.5, 15.7 and
15.8 Problems 13.42, 13.56, 13.58
58
TODAY (02/02)
NMRSpectroscopy (Principle and Application) (chemi
cal shift, splitting patterns )
Problems 13.65, 13.66
59
TODAY (01/31m)
NMRSpectroscopy (Principle and Application) (chemi
cal shift, splitting patterns )
Reading Assignment for Chapter 15 Sections 15.1
thru 15.10 with emphasis on 15.2, 15.5, 15.7 and
15.8 Problems 13.42, 13.56, 13.58
60
TODAY (01/28m)
NMRSpectroscopy (Principle and Application) (chemi
cal shift, splitting patterns )
Problems 13.51, 13.52(b), 13.55
61
TODAY (01/26m)
IR Spectroscopy (Principle and
Application) NMRSpectroscopy (Principle and
Application)
Problems 13.31, 13.37, 13.49
62
TODAY (01/27e)

• IR Spectroscopy (IR peaks )
• NMR (Principle and Application)

Problems 13.31, 13.37, 13.49
63
TODAY (01/25e)

• Mass Spectrometry (Determining Molecular Formula)
  
• IR Spectroscopy (Principle and Application)
• NMR (Principle and Application)

Problems 12.48 and 13.35
64
TODAY (01/20e)

• Quiz I Review
• Mass Spectrometry
• Principle and Application
• IR Spectroscopy
• Principle and Application

• Reading for next week 13.4 , 13.5, 13.7 thru
  13.11 and 13.13
• Problems 12.18, 12.21, and 12.28 thru 12.31

65
TODAY (01/24m)
Mass Spectrometry (Principle and Application) IR
Spectroscopy (Principle and Application)
Problems 12.48 and 13.35
66
TODAY (01/21m)
Quiz I Review Mass Spectrometry (Principle and
Application) IR Spectroscopy (Principle and
Application)
Reading for next week 13.4 , 13.5, 13.7 thru
13.11 and 13.13 Problems 12.10, 12.11, 12.14,
12.43, 12.51, 12.53,
67
TODAY (01/19m)
UV-Vis Spectroscopy (Principle and Application
) Mass Spectrometry (Principle and Application)
Reading Complete 12.1-12.7 and 13.1 13.3
Problems 12.18, 12.21, and 12.28 thru
12.31
68
TODAY (01/13e)

• Diels Alder Reaction
• Characteristics and Stereochemistry
• UV-Vis Spectroscopy
• Principle and Application

• Reading assignment
• Sections 12.1 - 12.7 and 13.1 13.3
• Scan sections 12.8 and 12.9
• Quiz I on Thurs( 1/20) , 14.16, 14.33, 14.34,
  14.40,
• Predict products /write a mechanism for a 1,4
  addition rxn and a DA rxn
• Describe stereochemistry of D-A
• Estimate the lambda max for a conjugated system
• Explain importance of HOMO and LUMO in UV-Vis
  spectroscopy

69
TODAY (01/14m)
Diels Alder Reaction (Characteristics and
Stereochemistry UV-Vis Spectroscopy (Principle
and Application )

• Reading assignment for next week
• Sections 12.1 - 12.7 and 13.1 13.3
• Scan sections 12.8 and 12.9
• Do problems 14.45 and 14.53
• Quiz I on Fri( 1/21)
• Predict products /write a mechanism for a 1,4
  addition rxn and a DA rxn
• Describe stereochemistry of D-A rxns
• Estimate the ?max for a conjugated molecule
• Explain importance of HOMO and LUMO in UV-Vis
  spectroscopy

70
TODAY (01/18e)

• UV-Vis Spectroscopy
• Principle and Application
• Mass Spectrometry
• Principle and Application

• Quiz I on Thurs( 1/20)
• Problems
• 14.45, 14.53 ( circle the chromophore in the
  given molecule in 14.53 )
• 12.18, 12.21, 12.28 thru 12.31

71
TODAY (01/14m)

• Diels Alder Reaction
• Characteristics and Stereochemistry
• UV-Vis Spectroscopy
• Principle and Application

Problems 14.45, 14.53 ( circle the chromophore
in the given molecule in 14.53 )
72
TODAY (01/11e)

• Conjugation and Stability in Dienes
• 1,2 versus 1,4-addition ( kinetic vs
  thermodynamic control )
• Diels Alder Reaction
• Comments on the Course Syllabus
• UV-Vis Spectroscopy

• Reading assignment for this week
• Sections 14.1-14.6 and 14.8 14.11 in McMurry
  
• Review sections 1.2, 1.12, and 5.7
• Work Problems 14.6 thru 14.9, 14.20, 14.22 ,
  14.32

73
TODAY (01/12m)

• 1,2 versus 1,4-addition ( kinetic vs
  thermodynamic control )
• Diels Alder Reaction
• UV-Vis Spectroscopy

• Reading assignment for this week
• Sections 14.1-14.6 and 14.8 14.11 in McMurry
  
• Review sections 1.2, 1.12, and 5.7
• Work Problems 14.6 thru 14.9, 14.20, 14.22 ,
  14.32

74
TODAY (01/10)

• Conjugation and Stability in Dienes
• 1,2 versus 1,4-addition ( kinetic vs
  thermodynamic control )
• Comments on the Course Syllabus
• Diels Alder Reaction
• UV-Vis Spectroscopy

• Reading assignment for this week
• Sections 14.1-14.6 and 14.8 14.11 in McMurry
  
• Review sections 1.2, 1.12, and 5.7
• Work Problems 14.6 thru 14.9, 14.20, 14.22 ,
  14.32

75
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