CEE 1 AY 2022-2023 v.

Phosphorus Containing
ORGANIC CHEMISTRY a. Phosphate Group
Handouts b. Organophsophates

Instructor: Jeritz George A. Orbigo RPh PROPERTIES OF HYDROCARBONS

1. Stability of the Carbon Atom
ORGANIC COMPOUNDS a. Octet Rule
- Derived from carbon 2. Hybridization
- Can be synthesized by humans o Mixing of two or more non-
- UREA = the first organic compound equivalent atomic orbitals to form a
synthesized in the laboratory new set of equivalent or degenerate
orbitals
HYDROCARBONS (C and H only) o SIGMA BOND
a. Aliphatic Hydrocarbons o PI BOND
Saturated = Alkanes 3. Isomerism
Unsaturated = Alkenes and Alkynes o Existence of two or more
b. Aromatic Hydrocarbons compounds having same molecular
Benzene and Derivatives formula but different structures
o Aromatic Ring/Nucleus
Polycyclic Benzenoids/Polyaromatic Types of Isomerism
Hydrocarbons
o Benzene ring fused together Structural Stereoisomers
1. Naphthalene Aka Constitutional
Chain/Skeletal Geometric
- Branching - Diastereomers
- Double
bond/cyclic
2. Anthracene Positional Conformational
- Bond, - Open chain/cyclic
substituent,
functional
group
Functional Configurational/Optical
3. Benzo(a)pyrene
- Different - Optical Activity
o Procarcinogen, undergoes Phase 1
Functional - Enantiomers
Metabolism
Group
o Soot, cigarette, smoke, grilled food
o Epoxide derivative (carcionogenic)
A. STRUCTURAL/CONSTITUTIONAL ISOMERS
Different orders of bonding
HYDROCARBON DERIVATIVES
i. Chain/Skeletal
i. Halogen Containing
- alkanes, branching
a. Alkyl Halides
b. Aryl Halides
BUTANE ISOBUTANE/METHYLPROPANE
ii. Oxygen Containing
a. Alcohols/Phenols
b. Ethers
c. Aldehydes
d. Carboxylic Acids
e. Carboxylic Acid Derviatives
1. Acid Halides
2. Acid Anhydrides
Note:
3. Esters
4. Amides
5. Nitrates
PENTANE ISOPENTANE NEOPENTANE
iii. Nitrogen Containing
a. Amines
b. Heterocyclic Nitrogen Compounds
- Alkaloids, purine, pyrimidine bases
Examples:
Pyridine
Melamine

Properties of Melamine
Note:

iv. Sulfur Containing

a. Thiols
b. Thioethers
ii. Positional Note: Index of Hydrogen Deficiency (IHD)
- differ in position of multiple bond,
substituent or functional group Formula:

1-BUTANE 2-BUTANE

- Tells the sum of multiple bonds + rings that

may be present, but does not specify
exactly how many multiple bonds or rings
CYCLOBUTANE METHYLCYCLOPROPANE are present

Ex: C4H8 C6H6

1-BROMOPROPANE 2-BROMOPROPANE

B. STEREOISOMERS
- different spatial orientation/ arrangement
of atoms

i. Geometric
- double bond/alkene: Cis/Trans E/Z
- cyclic: cis, trans
Disubstituted benzene - aka diastereomers
- Ortho (1,2)
- Meta (1,3) Alkene
- Para (1,4)
2-butene

1-butene

Butenol
E=
Z=
iii. Functional
- Different functional groups

____________
- Alcohol:
- Ether:
Note: CAHN-INGOLD-PRELOG Sequence
-
____________
- Aldehyde:
- Ketone:

____________
- Carboxylic Acid:
- Ester: Cyclic
1,2 – dibromocyclobutane
ii. Conformational C. CONFIGURATIONAL/OPTICAL
- Open chain: rotation along a single bond - optical activity; “enantiomers”
- Cyclic: ring flipping
o Rotation along a single bond Dextrorotarory = d (+)
Levorotatory = lambda (-)
ETHANE
Note: How to determine if a structure is optically
active or not?

1. Find chiral center

2. No symmetry element
1. Saw-Horse Projection Perspective Formula
(Dash and Wedge) Enantiomer:
Diasteromers:
Meso Compounds:

2. Newman Projection

+ Stability of Conformation:
1. Tortional Energy = Energy needed to resist
rotation
Note:
2. Steric effect/Crowding – presence of bulky
groups

= Increase stability: Eclipse 1 < Eclipse 2 < Gauche

staggered < antistaggered Cis and Trans with chiral caron
Cis = forms meso compound
Trans – forms enantiomers
More stable conformation
Cyclobutane

Cyclopentane

Cyclohexane
HYDROCARBON AND DERIVATIVES 1. HALOGENATION: Free Radical Substitution
REACTIONS

ALKANES

#C Rootword Alkane Formula

1
2
3
4
5
6
7
8 Chain Reaction Mechanism
9 1. Chain Initiation
2. Chain Propagation
10
3. Chain Termination
11
12
13
14
15
16
17
18
19
20

SUBSTITUENTS
ALKENES
1. -R - Position of double bond + rootword (#C) +
-ene

2. -X

3. -OR
1. CATALYTIC HYDROGENATION (REDUCTION
Ex. Production of Margarine

4. -NO2

Rules on Naming Alkanes

2. HALOGENATION
3. HYDROHALOGENATION: Addition of HX ALKYNES
- Regioselective
- Markovnikov’s Rule

Reactions

1. CATALYTIC HYDROGENATION

4. HYDROHALOGENATION WITH ROOR (Alkyl

Peroxide)

2. HYDRATION

AROMATICS

5. HYDRATION

Reactions
1. NITRATION

6. OXIDATION

i. HYDROXYLATION/GLYCOL FORMATION
- Bayer’s Test for Unsaturation

2. HALOGENATION
ii. OXIDATIVE CLEAVAGE
3. FRIEDEL-CRAFTS ALKYLATION ALCOHOLS

Classification of Alcohols
a. Based on number of R Groups attached
Primary Alcohol

4. FRIEDEL-CRAFTS ACYLATION Secondary Alcohol

Tertiary Alcohol

b. Based on number of -OR

5. SULFONATION Monohydric
Dihydric
Trihydric
Polyhydric

Reactions
1. Lucas Test

Note: Group already present affects:

1. Reactivity 2. Reaction with Active Metals
2. Orientation of incoming electrophile

A. Ortho- and Para- directing ACTIVATORS

Strongly activating
Moderately activating 3. Dehydration
Weakly Activating

4. Oxidation

B. Meta-directing DEACTIVATORS
Strongly deactivating
Moderately deactivating

C. Ortho- and Para – directing Deactivators

Weakly Deactivating
ETHERS 3. Nitrogen Nucleophiles
Type of Ethers a. Rxn with primary amines = Imines
1. Open Chain
a. Symmetrical Ethers

b. Rxn with secondary amines =

Enamines

b. Mixed Ethers
c. Rxn with tertiary amines = NR

2. Cyclic Ethers
a. Epoxides/Oxiranes/Oxacyclopropanes

d. Imine Derivatives

b. With more than 3 members

4. REDOX Reactions
a. Benedict’s Test

ALDEHYDES AND KETONES

Aldehydes

b. Tollen’s Test/Silver Mirror Test

Ketones

c. Iodoform Test

REACTIONS
1. Carbon Nucleophiles
a. Reaction with CN-

Pharmaceutical and Industrial Agents

i. Formaldehyde
ii. Benzaldehyde
iii. Vanillin
iv. Chloral Hydrate
v. Acetone
b. Grignard Reagent vi. Cholacetophenone
vii. Pepper Spray
viii. Muscone

CARBOXYLIC ACIDS

2. Oxygen Nucleophiles

Reactions
1. Neutralization
2. Conversion to Acid Derivatives AMINES
a. Acid/Acyl Chlorides

1. Aliphatic and Aromatic Amines

b. Ester

c. Amides

3. Reduction
REACTIONS
1. Neutralization/Salt Fromation

2. Diazotization
ACID DERIVATIVES
1. Acid/Acyl Chlorides

2. Acid Anhydrides

3. Esters

4. Amides