Organic Chemistry 144 Basics – Foundational Concepts, Functional Groups, and Reaction Mechanisms (Lecture Summary)

Lone pairs
Bonding Pairs :
Homologous Series :




Series of
·
compounds that differ only in CH2 groups.
c) -
: : >
-



Lone pairs : ↳
Physical properties compareable
-




only found
&
on one atom
↳
Only van der Waals forces
Bonding pairs
Shared
:

↳ Boiling point increases as chain length increases
e

↳ Non-polar (not soluble in water) (soluble in non-polar solvents)
of bond
or
pairs-18-groupor

Sigma (s)$Pi (i) bonds Isomers :




same molecular formula but different 3p arrangement

·
·




·
win :


T T
Constitutional isomers Conformers
·
same molecular formula , but Different 3D arrangement
Formal charge : atoms bonded in different of atoms in molecule due to
order rotation about single bonds
F = Valence e -


Clone pair e + (t bond pair
.

eJ] Eg Chiz
:
Eg CsHiz
:




Hybrid Orbitals :




·
Orbitals 'mix' to form new orbitals with equal energies -- called degenerate orbitals
↳ Process =

hybridisation
↳ wher 2 orbitals mix Form z new orbitals ,
exc .

↳ When orbitals
hybridise is causes bond to have same
energy Nomenclature : Prefixes..
4 : Met

·
Hybrid orbitallinear geometry
Sp ·
Parent How many c in longest chain
: 2 : Et


·
Sp Hybrid orbital trigonal planar geometry ·
Suffix Type of compound (alkane, alcohol etc
: 3 : Prop


·
Sp3 Hybrid orbital tetrahedral geometry
=> ·
prefix : which are attached to the chain
groups 4: But

5: Pent

① parent with longest chain
Always use 6: Hex


Hydrocarbons : ② Choose longest chain with most substituents : Hept

Cif = + same length) 8 :
Oct


Hydrocarbon H
③ start numbering closest to 1st substituents a

10 :
: Non
Dec

, Benzyl vs Phenyl Ethers :
Acetals &Hemi-acetals :
Imin
I




·
Hetero-atom Functional group R-O-R ·
Hemi-acetal : (with single bonds to ·
-


=N-
Benzene :
onenyl group : ↳
R-group carbons may have no other 20's ,
where 10 is · -


C = N

hetero-atoms bonded to it
.
part of an OH group

LR-group carbons must be sp Imine :
h 8lt O of
O
Benzyl group :
O
Phend :
ether
diethyl tetrahydrofuran(HF)
·
Acetal (with single bonds
: to 20's
, Nitrile :




Abbreviations forSubstituents none part of ou
group
Amines :
O
O
·

Group name ·
Abbreviation
methyl Me R- group carbons other O bo
may have no
· ·




ethyl Et hetero-atoms bonded to it lether
(0, ) ·
it bon

propyl Pr loR-group carbons must be sp
isopropyl iPr ↳ Amines =
weak bases

butyl Bu/nBu ↳ Protonated amines are weak
Carboxylic acids :
isobutyl iBu acids

sec-butyl sBu/s-Bu ·
R group-oH group 3 other R group
"Propylamine
tert-butyl -Bu/x-Bu ① Primary amine , 1 NAz Bonded to 1 R
group starts with C
"

Phenyl Pr and 2 hydrogens ↳ Suffix =
"-oic acid
amine to

① secondary amine, zo diethyl Bonded to 2 R groups Lo Suffix for ester-"-ester"
and 1 hydrogen ↳ Carboxylic acid can form ester
triethylamine
Alcohols : ⑤ Tertiary amine , 3" Bonded to 3 R
groups
and Vice Versa
N
acid: weak
and no hydrogen Lo carboxylic organic acid
R-OH

Aldehydes B Ketones
O
carbon may have
↳
R-group not :


bonded to it R
any heteroatoms - R O
↳
R-group carbon must be sp hybridised · =
0


↳ sp hybridisation
R R ·

Carboxylic Acid :



Classification Lo polarity effects
·
:
reactivity g



① Primary 1Kohol -a Primary alcohol bonded LSuffix of aldehyde-a
Ot
ethand carbon Ketone
↳Suffix
to primary to :
-one

of stem,
Secondary alcohol is bondedIf aldehydelketone
isopropand
Secondary zo alcohol not part
o indicated with "oxo" Esters
secondary carbon it is :
to a . ·