5/1/2018

GENERAL OVERVIEW
History
Jons Jacob Berzelius
Organic Chemistry Theory

Friedrich Wohler
Rowel P. Catchillar, MS

The Carbon Atom Carbon Characteristics

Configuration:
Group: Catenation
Period:
Atomic number:
Chemical bond:

Carbon Characteristics Hybridization

Hybridization: Structure 1

Types of Bond
Sigma Structure 2
sp3

sp2

sp
Pie Bond Structure 3

1
 5/1/2018

Geometry Shape Prediction

Bond Angle Shape Prediction Predict the shape of:
Single Bond Formula: H2O
NH3
CH4
Double Bond

Triple Bond

Shape Prediction Nomenclature System

Common Derived IUPAC
Source:
Discoverer:
Prefixes
(1)

(2)

(3)

IUPAC System Prefixes Common vs IUPAC

No. of C Prefix No. of C Prefix No. of C IUPAC No. of C Common

atoms atoms atoms atoms
1 6 1 1
2 7 2 2
3 8 3 3
4 9 4 4
5 10 5 5

2
 5/1/2018

Hydrocarbons Saturated Hydrocarbon

Composition Alkanes vs Alkyl group
Combustion process aka
Bonds:
Types
Bond Types:
Aliphatic
Hybridization:
General formula:
Aromatic
Properties:
◙ (1)
Alicyclic or carbocyclic

Alkane Nomenclature Which is correct

Parent (prefix + -ane)
Substituents
Same
Different

Common mistakes Common mistakes

3
 5/1/2018

Correct or incorrect? Saturated Hydrocarbons

2,3-dimethylpentane Cycloalkanes
1,2-dimethylbutane Carbon rings
Gen. formula:
4-methyl-3-ethyl-octane
Nomenclature:
◙ cyclo + alkane name

Unsaturated Hydrocarbons Unsaturated Hydrocarbons

Alkenes Nomenclature Alkadienes: 2 carbon-carbon
aka -ene double bonds;
Bonds: Double bond position + prefix + diene
Bond Types:
1,3-butadiene
Hybridization:
General formula:
 Isoprene units

Unsaturated Hydrocarbons Aromatic HCs

Cycloalkenes Pleasant odor possessed by there
Carbon ring with double bond substances
General Formula: Parent:
Alkynes Isolated by M. Faraday
aka August Kekule:
Triple bonds
Type of bond
General Formula Hybridization:

4
 5/1/2018

The Aromaticity Rule Examples

Huckel’s Rule: 4n + 2 = πe Benzene
1,3,5-hexatriene
Aromatic or Antiaromatic
Cyclobutadiene
(1) Structure:
(2) Double bond:
(3) Hybridization:
(4) Shape: p
Note: Atom with one or more
Non-aromatic lone pairs attached to an sp2
hybridized orbital becomes sp2
also

Monosubstituted benzenes Monosubstituted Benzenes

Toluene  Benzaldehyde
 Nitrobenzene
 Ethylbenzene
 Chlorobenzene
 Bromobenzene Phenol  Benzoic acid

 Aniline

Disubstituted benzenes Polysubstituted benzenes

Use prefixes, Parent: Monosubstituted benzenes
Ortho –  Examples
Meta –
1,3,5 – trinitrobenzene
Para –
 What is the name of the structure?

5
 5/1/2018

Polycyclic aromatic compounds /

Fused aromatic ring system
Correlation: Pheromones
Napthalene
Pheromones
 Anthracene
Aggregation
 Phenanthrene Attraction
Tetracene Alarm
 Pyrene Examples
2-methylheptadecane (tiger moth)
Undecane (cockroaches)
Correlation: Benzopyrene
Methyl-p-hydroxybenzoate

Reaction Mechanism
Markovnikov’s Rule
Application: hydration, halogenation ALCOHOLS, PHENOLS,
THIOLS, AND ETHERS
Example: Preparation of isopropyl alcohol

Alcohol Alcohol Nomenclature

Carbine group OH group Common names
Name of alkyl group + alcohol
Derived name
carbinol (an old name of methanol)
IUPAC rules
Include –OH group in the parent chain
–OH is given the lowest possible number
Name ending in –ol

6
 5/1/2018

Alcohol Nomenclature Alcohol Oxidation

Structure Primary alcohol

Common
Secondary alcohol
Derived
IUPAC

Tertiary alcohol

Examples Thiols
Ethanol Aka:
Isopropyl alcohol Naming: same as alcohol but –ol suffix
Glycerol is replaced by –thiol
Ethylene glycol Properties
foul odor
oxidized to disulfide
Example: Alliin  allicin

Examples Phenol
methanethiol Formula:
group aka
2-butanethiol Properties
Form ion –dipole and hydrogen bonds
Enhance water solubility
2,3-dimercapto-1-propanol
Esterified to form prodrugs
aka
Susceptible to oxidation

7
 5/1/2018

Examples Ethers
Catechol 1-naphthol ROR
Nomenclature
Derived Name: yl + ether
IUPAC: alk”oxy” + parent alkane name
Resorcinol
2-naphthol

Hydroquinone

Classification
Classification
Open-chain (Symmetric or asymmetric)

Ring / Cyclic

Name the structures given

Structure Derived IUPAC

THE CARBONYL GROUP AND

CARBONYL-CONTAINING
COMPOUNDS

8
 5/1/2018

Aldehydes & Ketones Reaction

General Formula: CnH2nO ALDEHYDES:
Oxidized to ______ & reduced to ______
Functional isomers
KETONES:
Aldehydes: RCHO Reduced to ______
Ketones: RCOR

Nomenclature of Aldehydes Nomenclature of aldehydes

IUPAC
Longest chain w/ aldehyde + -al Common Derived IUPAN
Aldehyde group not numbered
Common name
#C + aldehyde
Derived name
Alkyl group + aldehyde
Examples of aldehydes:
Vanillin
formaldehyde

Nomenclature of ketones Ketones

Name Derived IUPAC
IUPAC:
Parent chain w/ ketone group (lower number) CH3COCH3
Ending: –one
Derived: Alkyl name + ketone

Pentanone isomers

9
 5/1/2018

Test for Aldehydes and Ketones

Tollen’s Test

Benedict’s Test
Fehling’s Test

Carboxylic acid
Functional group
Nomenclature
IUPAC
Common
◙Formic acid
◙Acetic acid
◙Butyric acid
Greek Prefixes

Classification Classifications
Monocarboxylic acid Dicarboxylic acid Aromatic
(1)Saturated carboxylic acid

(2)Unsaturated

10
 5/1/2018

Classifications Carboxylic acid Derivatives: Esters

Hydroxyacids Amino acids Synthesis:

Degradation:
Properties
Pleasant odor (fruity odor)
Unpleasant when hydrolyzed

Carboxylic acid Derivatives: Anhydrides Carboxylic acid Derivatives: Amides

Functional Group:

Examples
Urea
Beta-lactam ring

Amines
Classification
Primary

Secondary
ORGANIC NITROGEN COMPOUNDS:
AMINES AND AMIDES Tertiary

11
 5/1/2018

Alkaloids Amine Nomenclature

Naturally occuring amines Primary: alkanamines

Ethylamine

Isopropylamine

cyclohexylamine

Amine Nomenclature Amine Nomenclature

Aromatic amines Secondary & Tertiary (Derived)
Aniline
metachloroaniline

Amine Nomenclature
Secondary and tertiary (IUPAC)

12
 5/1/2018

Stereoisomers

Same (1)
Same (2)
Different
STEREOCHEMISTRY

Chirality Optical Activity:

Handedness Instrument: __________
Non-superimposable Rotations:
Chiral Carbon ◙Clockwise: _________
aka ◙Anticlockwise: __________
Definition: ◙Racemic
Hybridization:
Shape:
Optical activity:

Polarimeter Configuration of Chiral Carbon

Cahn-Ingold-Prelog System
R-configuration
S-configuration
Fischer-Rosanoff System
D-configuration
L-configuration

13
 5/1/2018

Comparison Cahn-Ingold-Prelog System

Depends on
Parameter R/S D/L
Aka Cahn-Ingold Prelog Fischer-Rosanoff
System System
Configuration
Labels

3D terms Simple Trick

Back
Solid Front
Wedge
Dash
Side

Lactic Acid Thalidomide

14
 5/1/2018

Isomers Structural Isomers

Same molecular formula Isomer Same MF but differ Examples
in…
Different …
Chain Carbon arrangement
isomers
Position Unsaturated bond
isomers location
Functional Functional group
isomers

Stereoisomers Conformational Isomers

Isomer Types Involves single bond only
Geometric Cis Sawhorse representation
Isomers Trans Newman Projection
Optical Isomers Enantiomers Ring conformations
Diastereomer Ball and stick model
Meso compounds
Conformational
isomers
Tautomers

Sawhorse and Newman Ring conformation

15
 5/1/2018

Tautomerization
tauto “same”; meros “part”
Special kind of isomerism
Rapid interconversion between two
substances
KETO-ENOL TAUTOMERS
Eg. Propanone to 2-propanol

16