Chemistry II

SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Dr. rer. nat. Filiana Santoso

Phone: 021 – 3045 0045
HP: 0815 - 970 17 72
Email: filiana.santoso@sgu.ac.id
4th Floor, Room FA 401
Wenn Du Fragen hast, komm‘ einfach vorbei

February 8, 2021 Filiana Santoso 1

 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Chapter 1: Covalent Bonding

& Functional Groups in
Organic Chemistry

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Organic Chemistry (OC)

• The study of the compounds of carbon.
• C always has “four hands”.
• It can form single, double, and triple bonds.
H C C H
C2H2 (10)
Acetylene

O
H H H
C O H C H
C C O
O
H H
H
C2H4 (12) CH2O (12) H2CO3 (24)
Ethylene Methanal Carbonic acid

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Bonds in OC
• In neutral molecules containing C, H, N, O, and halogen
– H has 1 bond
– C has 4 bonds and no free electron pair
– N has 3 bonds and 1 free electrons pair
– O has 2 bonds and 2 free electrons pairs
– F has 1 bond and 3 free electrons pairs

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Resonance Structure
• For many molecules and ions, no single Lewis structure
provides a truly accurate representation.
• Examples:

Nitrite ion O O
(equivalent
N N
contributing
structures) O O

Ethanoate ion O O
(equivalent
contributing CH3 C CH3 C
structures) O O
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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Curved Arrow
• Curved arrow:
arrow a symbol used to show the redistribution of
valence electrons
• In using curved arrows, there are only two allowed types of
electron redistribution:
– from a bond to an adjacent atom
– from an atom to an adjacent bond
• Electron pushing by the use of curved arrows is a survival
skill in organic chemistry
• Learn it well!

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Functional Groups
• Functional group:
group an atom or group of atoms within a
molecule that shows a characteristic set of physical
and chemical properties
• Functional groups are important for three reasons,
they are
– the units by which we divide organic compounds
into classes
– the sites of characteristic chemical reactions
– the basis for naming organic compounds
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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Hydroxyl Groups
• Hydroxyl (R–OH) group of alcohols
R = alkyl group = carbon chain

HH
H- C-C- O- H
HH
An alcohol
(Ethanol)
Ball and Stick Model Space Filling Model

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Amino Groups
• Amino group of 1° , 2°, and 3° amines
– 1° amine: R–NH2
– 2° amine: R2–NH
– 3° amine: R3N

CH3 N H CH3 N H CH3 N CH3

H CH3 CH3
(a 1° amine) (a 2° amine) (a 3° amine)
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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Carbonyl Groups
• Carbonyl group of aldehydes and ketones
– Aldehyde: R–CHO
– Ketone: R–CO–R
O O
CH3 -C-H CH3 -C-CH3
An aldehyde A ketone

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Carboxyl Groups
• Carboxyl group of carboxylic acids
Carboxylic acid: R–COOH
O
CH3 -C-O-H or CH3 COOH or CH3 CO2 H
Acetic acid

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

End Chapter 1
Covalent Bonding &
Functional Groups in
Organic Chemistry

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Chapter 2:
Acids and Bases

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Arrhenius Acids and Bases

• In 1884, Svante Arrhenius proposed these
definitions
– Acid: a substance that produces H3O+ ions (from
H+ and H2O molecule) in aqueous solution
HCl + H2O  H3O+ + Cl-

– Base: a substance that produces OH- ions in

aqueous solution
NaOH + H2O  Na+ OH-

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Brønsted-Lowry Acids & Bases

• Acid: a proton donor
• Base: a proton acceptor
+ -
:

: :

: :
H O H + :O H H O: + H O H
H H
Proton Proton
donor acceptor

H H
+ +
:
:

H O H + :N H H O: + H N H
H H H H
Proton Proton
donor acceptor
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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Strong Acids and Bases

• Strong acid: one that reacts completely or almost completely
with water to form H3O+ ions
• Strong base: one that reacts completely or almost
completely with water to form OH- ions
– Most common strong acids and bases are inorganic.
Formula Name Formula Name
HCl Hydrochloric acid LiOH Lithium hydroxide
HBr Hydrobromic acid NaOH Sodium hydroxide
HI Hydroiodic acid KOH Potassium hydroxide
HNO3 Nitric acid Ba( OH) 2 Barium hydroxide
H2 SO4 Sulfuric acid
HClO4 Perchloric acid

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Weak Acids and Bases

• Weak acid: a substance that dissociates only partially in
water to produce H3O+ ions
– Example: acetic acid in water, only 4 out every 1000
molecules are converted to acetate ions
-
CH3 COOH(aq) + H2 O( l) CH3 COO ( aq ) + H3 O+ ( aq)
Acetic acid Acetate ion

• Weak base: a substance that dissociates only partially in

water to produce OH- ions
– Example: ammonia
NH3 (aq) + H2 O( l) NH4 + (aq) + OH-( aq)
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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

What Determines Acidity?

• There are three factors:
– the electronegativity of the atom bonded to H
in HA
– the resonance stabilization of A-
– the inductive effect

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Electronegativity and Acidity

Greater electronegativity of the atom bearing the negative
charge:
 In the acid HA, its electrons are closer to A
 H+ can be released more easily
 HA is stronger acid
H3C—H H2N—H HO—H F—H

Electronegativity 2.5 3.0 3.5 4.0

of A in A-H
pKa 51 38 15.7 3.5

Increasing acid strength

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Resonance Stabilization and Acidity

– Greater resonance stabilization of the anion: higher acidity
– Compare the acidity of an alcohol and a carboxylic acid:
Alcohols are very weak acids: there is no resonance
stabilization in an alkoxide anion
+ H3 O+
-
CH3 CH2 O-H + H2 O CH3 CH2 O pKa = 15.9
An alcohol An alkoxide
ion
Carboxylic acids are weak acids: it has two equivalent contributing
structures for the carboxylate anion
- +
CH3 COOH + H2 O CH3 COO + H3 O pKa = 4.76
O O O
+
CH3 C + H2 O CH3 C CH3 C + H3 O

O H O O
The carboxylate anion is stabilized
by delocalization of the negative charge
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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Inductive Effect and Acidity

• Inductive effect: polarization of electron density
transmitted through covalent bonds by a nearby
atom of higher electronegativity.
• Greater inductive effect  higher acidity.
O O
- +
CH3 -C-OH + H2 O CH3 -C-O + H3 O pKa 4.76

O O
CF3 -C-OH + H2 O CF3 -C-O- + H3 O+ pKa 0.23

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Lewis Acids and Bases

• Lewis acid (electron acceptor): any molecule or ion
that can form a new covalent bond by accepting a
pair of electrons
• Lewis base (electron donor): any molecule or ion
that can form a new covalent bond by donating a
pair of electrons
- +
A + :B A B new covalent bond
Lewis formed in this Lewis
Lewis
acid base acid-base reaction

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Example of Lewis Acid-Base Reaction

CH3 O + H Cl CH3 O H + Cl
H H
Methanol An oxonium
Lewis base Lewis acid ion
(e- donor) (e- acceptor)

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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

Lewis Acid: Carbocation

• Another type of Lewis acid we will encounter in later chapters
is an organic cation in which a carbon is bonded to only three
atoms and bears a positive formal charge
– Also called as carbenium ion

bromine uses a lone

pair of electrons to form
a new bond to carbon
Carbocation

+ Br
CH3 -CH-CH3 + Br CH3 -CH-CH3
An organic cation Bromide ion 2-Bromobutane
(a Lewis acid) (a Lewis base)
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 Chemistry II
SWISS GERMAN UNIVERSITY Chapter 1 and 2: Introduction to Organic Chemistry

End Chapter 2

Acids and
Bases

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