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Chap. 12 Structure Determination: MS and IR

12.1-11.2 Mass Spectrometry
a) Basics

b) Mass spectrum

c) High-Resolution MS

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12.2-12.4 Fragmentation patterns (skipped)

12.5 Spectroscopy
a) Definition: the study of interactions between electromagnetic radiation and
molecules.

b) Principles

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12.6-12.7 IR Spectroscopy
a) Position of absorption

b) Intensity

c) Four regions

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12.8 IR spectra of some common functional groups

a) Hydrocarbons
Backbone of most organic compounds, only C-H and C-C
C-H
C-C
-1
Alkane (C-C)
28502960 cm
(8001300 cm-1)
Alkene (C=C)
30203100 cm-1
16401680 cm-1
Alkyne (CC-H)
3300 cm-1
21002260 cm-1
Internal CC
none
weak or none

b) Oxygen-containing compounds

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Chem 331

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Iowa State University

Chap. 13 Structure Determination: NMR

13.1-13.3 NMR spectroscopy
a) Basics:

b) Chemical shift

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c) Timescale

d) Operational issues

13.4-13.7 13C NMR

a) Position of absorption

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b) Intensities of the signals

c) DEPT

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d) Applications

13.8-13.10 1H NMR
a) Position of absorption

b) Equivalence test: replacement of two Hs with X, respectively

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c) Chemical Shifts

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c) Intensities

2
PPM

C5H12O (1:3)

2
PPM

4
PPM

C8H10 (2:3)

C6H12O (1:3)

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PPM

C6H12O (1:1)

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13.11-13.12 Spin-spin splitting (Multiplicity)

# of Hs on adjacent C
0
1
2
3
4
5
6

# of peaks in multiplet
1 (singlet)
2 (doublet)
3 (triplet)
4 (quartet)
5 (quintet)
6 (sextet)
7 (septet)

Area ratio
1
1 1
1 2 1
1 3 3 1
1 4 6 4 1
1 5 10 10 5 1
1 6 15 20 15 6 1

Give examples of OCH3, OCH2CH3, OCH(CH3)2, and OC(CH3)3

2
PPM

2
PPM

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PPM

PPM

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13.11-13.12 Solving structures using 1H NMR

PPM

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PPM

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2
PPM

2
PPM

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Iowa State University

PPM

PPM

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Iowa State University

Chap. 6 An Overview of Organic Reactions

6.1 Four basic types of Organic Reactions

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6.2-6.3 Radical Mechanisms

a) Mechanism

Half-headed curved arrows (fishhook) show movement of ONE electron

(radical reactions)
Full-headed curved arrows show movement of ONE PAIR of electrons (polar
reactions)
b) Radical reactions

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Chem 331

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6.4-6.6 Polar Mechanisms

a) Polarity vs Polarizability

b) Polar reactions (remember to follow the flow of electrons)

(The 3rd most important concept in organic chemistry)
E+ or E+ = electrophile or electron sink (Lewis acid), loves electrons (must
have empty orbitals for electrons)

Nu- or Nu = nucleophile or electron source (Lewis base), loves nucleus

(positive charge), rich in electrons

Electrons always go from Nu (electron source) to E (electron sink)

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6.7-6.10 Thermodynamic and Kinetics

a) Thermodynamics

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b) Calculation of H using Bond dissociation energy (BDE)

CH3H 438 kJ/mol

ClCl 243 kJ/mol
BrBr 193 kJ/mol
II 151 kJ/mol
c) Reaction rate theory

HCl 432 kJ/mol

HBr 366 kJ/mol
HI 298 kJ/mol

CH3Cl 351 kJ/mol

CH3Br 293 kJ/mol
CH3I 234 kJ/mol

d) Reaction energy diagrams

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Iowa State University

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Iowa State University

Chap. 7 Alkenes: Structure and Reactivity

7.1-7.2 Unsaturated compounds
Alkene (sp2)
Alkyne (sp)
Alkane (sp3)

Degree of unsaturation: CaHbOcNdXe

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7.3-7.5 Nomenclature
a) Rules for alkenes
Longest chain containing C=C
Number the chain to give lowest number to C=C
Number and name other substituents
Assign (E) or (Z) prefix as needed
E = entgegen = opposite
Z = zusammen = together = ze zame side the same side
Priority: higher atomic number (if tie, count next atom)
If double (or triple) bond, count twice (or three times)

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7.6 Stability of alkenes

a) Equilibrium

b) Heat of hydrogenation

c) General trend

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7.7-6.10 Electrophilic Addition of HX

a) Electrophilic addition reaction

b) Markovnikovs rule

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c) Carbocations (planar, sp2 hybridization)

7.10 Hammond Postulate

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Iowa State University

7.11 Carbocation Rearrangement

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Chem 331

Organic Chemistry

Iowa State University

Chap. 8 Alkenes: Reactions and Synthesis

8.1 Addition/Elimination
a) Dehydrohalogenation (-HX): Remove H and X on adjacent carbons only

b) Dehydration of alcohols (-H2O): Remove H and OH on adjacent carbons only

8.2-8.4 Addition reactions

a) General

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b) Addition of halogens

c) Halohydrin formation

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d) Addition of water

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Iowa State University

8.5-8.6 More Addition reactions

a) Hydroboration

b) Reduction/hydrogenation

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Iowa State University

8.7-8.8 Oxidation
a) Epoxide

b) OsO4 (osmium tetroxide)

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Iowa State University

c) Ozonolysis

8.9 Addition of carbenes

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Organic Chemistry

Iowa State University

8.10 Brief introduction of polymer

8.12-8.13 Stereochemistry of reactions

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