CHAPTER 1: ESSENTIAL CONCEPTS

Compendium of Essential Organic Chemistry Concepts, Techniques and Study

Hacks
Chapter 1: Essential concepts
Objectives:
To review relevant general chemistry concepts and relate its use throughout the
course of organic chemistry
To be familiar with organic chemistry terms and jargons
To understand the importance of understanding atomic structure
To differentiate atomic orbitals, hybridized orbitals, and molecular orbitals
To be proficient in drawing lewis structures
To realize/ recognize the existence of chemical trends and its importance in the
aspects of reactivity and related concepts

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Compendium of Essential Organic Chemistry Concepts, Techniques and
Study Hacks
1.1 ELEMENTS OF ORGANIC CHEMISTRY
There are a lot of texts which defines Organic chemistry as the study of
Hydrocarbons. Yet it is somewhat a period 2, p-block science.

H
Li

B B C N O
e
N M Al Si P S
a g

Practice:

H
e

l-----------P Block
elements---------------l

N
e
Ar

(halid
es)

CHONXSP (x=halides)
Important elements found in
organic substances
(memorize their atomic
weights, it would be handy
especially for Mass spec
which will be discussed
latter.)
BCNOF period 2 elements

Fill out the following table with the necessary data

Formula
weight

Electronic
Valence
Configurati eon

Formula
weight

Electronic
Valence
Configurati eon

B
2+

Mg

Cl

Li1+

Br

1.1.1 AN IMPORTANT ATOMIC TREND FOR ORGANIC

Stability of charges of the P-block Elements
Helps us understand:
Structure
2. Reactivity
1.

CHEMISTRY

Depends on:
1. Atomic size
Increasing
2. Electronegativity Increasing

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Compendium of Essential Organic Chemistry Concepts, Techniques and
Stability of negative charge
Study Hacks
Increasing because of EN
Increasing because of Size

the e- hence the more EN

B C N O F ENan holds
element is, the more stable the neg
charge
Cl
It is easier to contain moving electrons in
a larger space than in a smaller region
Br
for it minimizes charge repulsion.
Trend for Stability of positive charges just
the opposite direction
I Application of stability ofrunscharges
Practice:
1. Remember that bases are e- pair donors. Stable anions are not willing
to donate their e - hence they are_______(strong or weak?) bases
2. Draw the structures of the following species and rank them according
to anion stability : Methyl anion, fluoride, amide anion, hydroxide
<

<

<

Least stable

1.2 MOLECULAR

most stable

STRUCTURE AND REPRESENTATION

The structures of organic molecules (so as their reactivity) are governed by

quantum mechanical interactions. Quantum calculation however is not our major
concern. We are expected to at least make sense of these quantum mechanical
concepts (ie. Orbitals) and use them as justifications for our models of molecular
structures.
1.2.1 ATOMIC ORBITALS (AO) VS. HYBRID ORBITALS (HO) VS. M OLECULAR ORBITALS (MO)
Electrons need HOUSES we can view ORBITALS as ELECTRON HOUSES
Table 1.1 Orbitals that an orgchem student must know by heart
Atomic Orbitals

Hybrid Orbitals

Molecular Orbitals

(basic organic chemistry

often bothers only on pblock elements)

(for purposes of geometrical

simplicity)

(Combination of atomic
orbitals, useful for predicting
mechanisms, see chapter 4)

s,p

sp3, sp2, sp

,,n0, empty P, *,*

Hybrid states of carbon

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Chapter 1 and 2: Essential Gen Chem Concepts and Organic Representation

Hybridization of hetero atoms (NOX) follow ____________________.

What is the hybridization of the red oxygen

1.2.2 DRAWING MOLECULAR STRUCTURES
Counting octet and formal charges:
The electron configuration for period 2 atoms (Neon) is as follows:

1s2

Valence
shell for
Hydroge
n

2s2

2p6

Valence shell for

period 2 atoms
(B,C,N,O,F)
the basis of
octet rule

Octet rule 8 e- around period 2

atoms (4 e- pairs)
Hydrogen only 2 electrons ( 1 epairs)
Two types of e- pairs:

A:

Nonbonding /
Unshared/
Lone pair (LP)

Bonding
pair
(BP)

A-A

Counting octet of electrons:

Look at the O atom, count all of the electron pairs (ans : 2 LP +
2BP = 4 e- Pairs)
If there are 2 e- per pair, how many e- are there inside the circle
( ans: 8 e-)
Does the oxygen in the molecule follow octet (ans: yes, hence it

The structure is a MORTAL SIN IN ORGCHEM! Why?

Look at the H atom, count all of the electron pairs (ans : 2BP = 2
e- Pairs)
If there are 2 e- per pair, how many e- are there inside the circle?
Ans: ______

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Compendium of Essential Organic Chemistry Concepts, Techniques and
Eleven ways to draw an octet for period 2 atoms:
Study Hacks

These are the only drawings which

will give octet of electrons for the A
atom
So in summary to check for octet you
can:
1. Count all of the electron pairs
or
2. Check if it resembles these 11
drawings.

Formal charges: for period 2 atoms (including H) it ranges only between -1 to +1

Calculating/counting formal charges: Formal charge = Valence e- - total
electrons around
Atom
Val. e-

H
1

B
3

C
4

N
5

O
6

F
7

Notice that only half of the bond is in the circle, hence count 1eper bond
But both electrons are counted for each LP.
Valence electron for oxygen (from the table) =6
Total electrons around the atom = 6
Formal Charge = 6-6= 0

Practice:

Octet and Formal Charge

Assign the formal charge and determine which is plausible

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Chapter 1 and 2: Essential Gen Chem Concepts and Organic Representation
[ans:-2,-1,0,+1,+2; the first and last are not
plausible]

[ans:-1,-1,-1,+1; all are plausible]

Lewis Structure and Geometry
Draw the Lewis structure of the following compounds: CO2, O3, BH3, NH3, H2CO3,

CHAPTER 2: ORGANIC REPRESENTATIONS

2.1BOND-LINE

STRUCTURES

Practice: what is the molecular formula of the following compounds:

2.1.1. H OMOLOGOUS
Number
of
Carbons

SERIES

Condensed formula

Bondline structure

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1
2

Compendium of Essential Organic Chemistry Concepts, Techniques and

Study Hacks

3
4
5
6
7
8
9
10
2.1.2. F UNCTIONAL
NAME OF

GROUPS AND BASIC NAMING

FUNCTIONAL GROUP
C
A
E
T
A
A
N
A
K
A

PHENOL
T
A
I
E
S

STRUCTURE

(CAETA ANAK ATAI ES DAAA)

NAME AS
NAME AS
SUFFIX ___________
PREFIX____________

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Chapter 1 and 2: Essential Gen Chem Concepts and Organic Representation
D
A
A

PARTS OF SUBSTITUTIVE NOMENCLATURE

Stereioisomer
ism

2.2

Substituen
ts

Parent

Unsaturati
on

Main
FG

DETAILS IN ORGANIC REPRESENTATION

2.2.1 TYPES

OF

2.2.2 REACTIVE

C-ATOMS:

INTERMEDIATES

1.
2
3.
4.
2.2.3 FORMAL
Carbocations

CHARGE IN BOND LINE STRUCTURES

Oxygen

Nitrogen

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Compendium of Essential Organic Chemistry Concepts, Techniques and
Study Hacks
2.2.4. RESONANCE STRUCTURES AND PI-ELECTRON DELOCALIZATION
Cross check:
a. Consider hybridization of orbitals
b. Avoid breaking a single bond (only pi e- involved)
c. Never exceed octet for period 2 atoms

2.2.5 CONSTITUTIONAL ISOMERS

Constitutional isomers have same molecular formula, same hydrogen deficiency
index (HDI) and should be neutral (zero formal charge).

HDI =

Practice:

2 C+ 2H X + N
, where 1 HDI= 1 bond, or 1 ring
2

Draw all of the constitutional isomers with the molecular formula

1.) C5H8 , 2.) C3H6O2

Answers: