INTRODUCTION TO ORGANIC CHEMISTRY SUMMER ELECTIVE COURSE
with Adrian Dingle @ The Westminster Schools in 2011
adriandingleschemistrypages.com


DATES FOR ORGANIC ELECTIVE SUMMER 2011
WEEK 1
All days 8am-1pm
DAYMON 6/6TUE 6/7WED 6/8THU 6/9FRI 6/10
MOLECULE OF THE DAY
METHYL ISOCYANATE
Structure
NEWS ITEM
REF 1
REF 2
COCAINE
Structure
NEWS ITEM
REF 1
REF 2
VIAGRA
Structure
NEWS ITEM
REF 1
REF 2
THALIDOMIDE
Structure
NEWS ITEM
REF 1
REF 2
ETHYL METHANOATE
Structure
NEWS ITEM
REF 1
REF 2
WEEK 2
All days 8am-1pm
DAYMON 6/13TUE 6/14WED 6/15THU 6/16FRI 6/17
MOLECULE OF THE DAY
CAPSAICIN
Structure
NEWS ITEM
REF 1
REF 2
ETHYLENE-VINYL ACETATE
Structure
NEWS ITEM
REF 1
REF 2
TESTOSTERONE
Structure
NEWS ITEM
REF 1
REF 2
ALLICIN
Structure
NEWS ITEM
REF 1
REF 2
OXYCODONE
Structure
NEWS ITEM
REF 1
REF 2
WEEK 3
All days 8am-1pm except 6/25, 8am-11am (Exam)
DAYMON 6/20TUE 6/21WED 6/22THU 6/23FRI 6/24 (EXAM ONLY)
MOLECULE OF THE DAY
PROZAC
Structure
NEWS ITEM
REF 1
REF 2
NICOTINE
Structure
NEWS ITEM
REF 1
REF 2
CHOLESTEROL
Structure
NEWS ITEM
REF 1
REF 2
LIPITOR
Structure
NEWS ITEM
REF 1
REF 2
ORGANIC ELECTIVE RESOURCES
TOPIC NOTES HOMEWORKS TESTS TEXT RESOURCES TOOLBOX
1

NOMENCLATURE

NOTES
#1: Organic Worksheet 1a
- Nomeclature

Due: 6/8

Test: TOPIC 1

Test date: 6/8



Click here for a study guide to the test

Multiple-Choice Tests
A B C
PagesConceptProblems

p43-49Alkane & Halogeno Nomenclature2.1, 2.2, 2.3, 2.4, 2.6, 2.7, 2.8

CHAPTER 2 ANSWERS

p55-69Cycloalkane Nomenclature2.10, 2.11, 2.12, 2.26, 2.27, 2.28, 2.29, 2.30

CHAPTER 2 ANSWERS

p77-115Alkene and Alkyne Nomenclature3.3, 3.4, 3.34, 3.35 (a-e, i-j)

CHAPTER 3 ANSWERS

p125-145Aromatic Nomenclature4.7, 4.8, 4.20(a-e, g, i, l-m), 4.21 (a-b, d, f, h)

CHAPTER 4 ANSWERS

p209-231Alcohol Nomenclature7.1, 7.2, 7.26 7.27 (a-f, i-j), 7.29

CHAPTER 7 ANSWERS

p255-282Aldehyde & Ketone Nomenclature9.1, 9.2, 9.30 (a-f, h, i), 9.31 (a-e, g, i-j)

CHAPTER 9 ANSWERS

p287-321Carboxylic Acid Nomenclature10.1, 10.2, 10.37 (a-c, i-k), 10.38

CHAPTER 10 ANSWERS

p300Ester Nomenclature10.14, 10.15

CHAPTER 10 ANSWERS

p322Acid Halide Nomenclature10.44 (i)

CHAPTER 10 ANSWERS

p312Amide Nomenclature10.31

CHAPTER 10 ANSWERS

p327-350Amine Nomenclature11.2, 11.3, 11.4, 11.24 (a-i, k-l), 11.25 (a-f)

CHAPTER 11 ANSWERS
LABS

Organic Lab 1a
- Nomenclature Models


MSU PROBLEM SET 1A

GQ 1
- Valency

GQ 3
- Line/Condensed formula

GQ 4 (Q1-8)
- Line formula

GQ 6
- Formula and Nomenclature

GQ 11
- Structure and fomula

GQ 15
- Hybridization

GQ 18
- Functional groups

GQ 19
- Functional groups


MSU PROBLEM SET 1B

N1
- Nomenclature

N2
- Alkane nomenclature

N3 (Q1a-c; 2a-b; 3a-e; 4#3&5; 5#1&2; 6a-f; 7a-d;8a-c)
- Nomenclature

N4
- Nomenclature rings

N12
- Nomenclature alcohols

2

ISOMERISM

NOTES
#2: Organic Worksheet 2a
- Isomerism

Due: 6/10

Test: TOPIC 2

Test date: 6/10



Click here for a study guide to the test

Multiple-Choice Tests
A B C
PagesConceptProblems

p18-21Structural Isomerism1.17, 1.20, 1.38, 1.39, 2.31

CHAPTER 1 ANSWERS

p52-54Conformers2.9

CHAPTER 2 ANSWERS

p79-82Geometric (cis/trans) Isomerism3.6

CHAPTER 3 ANSWERS

p146-152Optical Isomerism5.2, 5.3, 5.4, 5.5

CHAPTER 5 ANSWERS

p152-157R-S Convention5.10, 5.11

CHAPTER 5 ANSWERS

p157-158E-Z Convention5.12, 5.13

CHAPTER 5 ANSWERS
WORKSHEETS

Organic Worksheet 2b
- Chemsketch

MSU PROBLEM SET 2A

C&SC 2(1)
- Isomers

C&SC 3
- Conformers

C&SC 7
- Alkene isomers

C&SC 8
- E/Z

C&SC 13(Part 2 A&E)
- R/S

C&SC 16(2, 4, 6, 8)
- R/S

FGR 5
- Halogenation

FGR 7
- Halogenation

3

MECHANISMS

NOTES
#3: Organic Worksheet 3a
- Mechanisms

Due: 6/14

Test: TOPIC 3

Test date: 6/14



Click here for a study guide to the test

Multiple-Choice Tests
A B C
PagesConceptProblems

p64-72Homolytic Free Radical Substitution2.19, 2.23, 2.24, 2.25, 2.46, 2.47, 2.48

CHAPTER 2 ANSWERS

p85-118Heterolytic Electrophilic Addition3.8, 3.9, 3.10, 3.11, 3.12, 3.13, 3.14, 3.15, 3.40, 3.41, 3.60

CHAPTER 2 ANSWERS

p146Heterolytic Electrophilic Substitution4.28

CHAPTER 4 ANSWERS

p191-204Heterolytic Nucleophilic Substitution6.6 (first part), 6.8, 6.11, 6.12 (a, c, h)

CHAPTER 6 ANSWERS
WORKSHEETS

Organic Worksheet 3b
- Mechanisms with ChemSketch


ANIMATIONS

Free Radical Substitution
- Halogens with alkanes

Electrophilic Substitution
- Nitration of benzene

Electrophilic Addition
- Addition to alkenes

Electrophilic Substitution
- Substitution in benzene

Electrophilic Addition
- Addition to alkenes

SN1
- 3o Haloalkanes with nucleophiles

SN1
- 3o Haloalkanes with nucleophiles

SN2
- 1o Haloalkanes with nucleophiles

SN2
- 1o Haloalkanes with nucleophiles

SN2
- 1o Haloalkanes with nucleophiles


MSU PROBLEM SET 3A

M3(1-8)
- Curly arrows

M4(1-3)
- Curly arrows

EN 2
- Electrophiles

EN 3
- Nucleophiles

GQ8 (1-5)
- Polarity

GQ15(A-F)
- Hybridization

GQ16
- Hybridization

GQ17
- Hybridization

4

REACTIONS

NOTES
#4: Organic Worksheet 4a
- Reactions I

Due: 6/17

Test: TOPIC 4

Test date: 6/17



Click here for a study guide to the test

Multiple-Choice Tests
A B C
PagesConceptProblems

p199Reaction #16.9

p186Reaction #26.1 (a), 6.2 (a)

p304Reaction #310.19

p210-222
p257
Reaction #47.3, 7.19, 9.3, 9.4

p271Reaction #59.20

p64-66Reaction #62.19, 2.20, 2.21

p85-91Reaction #73.8, 3.9, 3.10, 3.11, 3.13, 3.14

p213-214Reaction #87.14 (a)

p218Reaction #97.16, 7.17

p338Reaction #1011.17

p308Reaction #1110.22

p146Reaction #124.28 (a)

p147Reaction #134.36 (g)

p321Reaction #1410.42 (c)

p186Reaction #156.2 (b), 6.2 (c)

p266-267
p296
Reaction #169.14, 9.15, 10.10, 10.11

p308Reaction #1710.22

p299Reaction #1810.13 (one route)

p333Reaction #1911.10

-Reaction #20-

-Reaction #21-
LABS

Organic Lab 4b
- Preparation of Alcohol


WORKSHEETS

Organic Worksheet 4b
- Stars of Reaction I

Organic Worksheet 4c
- Stars of Reaction II

MSU PROBLEM SET 4A

FGR8 (R+R => ?, HCl & Br2 for all three compounds)
- Addition to alkenes

FGR33 (reagent on rows 4, 5, 7 & 11)
- Reactions of propanal

FGR35 (Jones', NaBH4 and C6H5MgBr for all three compounds)
- Reactions of carbonyl compounds

FGR37 (Butanoic + 1st row of reagents)
- Reactions of butanoic acid

FGR38 (1st two reactants, single step with LiAlH4, SOCl2, KOH, C2H5OH)
- Carboxyl derivatives

FGR39
- Carbonyl compounds

5

STRUCTURE DETERMINATION

NOTES
#5: Organic Worksheet 5a
- Structure Determination

Due: 6/21

Test: TOPIC 5

Test date: 6/21



Click here for a study guide to the test

Multiple-Choice Tests
A B C
PagesConceptProblems

p358-3801H NMR Spectroscopy12.1, 12.2, 12.3, 12.4, 12.5, 12.8, 12.19, 12.20, 12.21, 12.22

p376-386Mass Spectrometry12.16, 12.17, 12.41, 12.42, 12.45, 12.47

p370-384IR Spectroscopy12.12, 12.30 (first part), 12.34, 12.36
LABS

Organic Lab 5a
- Silver Mirror (Micro)

Organic Lab 5b
- Silver Mirror (Bottle)


VIDEO CLIPS

Tollen's reagent (Silver Mirror)
- Test for reducing group (aldehydes)
Fehlings Solution (Aldehydes)
- Test for reducing group (aldehydes)
2,4-DNP (Aldehydes & Ketones)
- Test for carbonyls (aldehydes & ketones)
Bromine & Potassium Manganate(VII) Test for unsaturation
- Test for unsaturation (double & triple bonds)
Iodoform Test (CH3 groups in -OH and -C=O)
- CH3C=O and CH3C(OH)-

MSU PROBLEM SET 5A

FGR4
- Combustion analysis

SPEC1
- Equivalent C and H atoms

SPEC2
- Equivalent C and H atoms

SPEC3
- NMR

SPEC4
- NMR

SPEC5
- Spin-spin splitting

SPEC6
- IR versus NMR

SPEC8
- NMR

SPEC12
- Mass Spec

SPEC19
- IR


MSU PROBLEM SET 5B

NMR-CTP
- H NMR Problems


MSU PROBLEM SET 5C

St. PETURSBURG NMR
- H NMR Problems


6

SYNTHESIS

NOTES
#6: Organic Worksheet 6a
- Synthesis

Due: 6/23

Test: TOPIC 6

Test date: 6/23



Click here for a study guide to the test

Multiple-Choice Tests
A B C
PagesConceptProblems

p139-148Directing Groups4.16 (b), 4.17 (first part), 4.36 (h), 4.39 (b)

MSU PROBLEM SET 6A

SYN3 (2 & 3)
- Synthesis

SYN13
- Directing groups

TOPIC NOTES HOMEWORKS TESTS TEXT RESOURCES TOOLBOX

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