ORGANIC CHEMISTRY

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 REFERENCES
Major references
[1] Phan Thanh Sơn Nam, Trần Thị Việt Hoa, ‘Organic Chemistry’, VNU-HCM Publisher,
2013, Call No. 547.07 PH-N
[2] Phan Thanh Sơn Nam, ‘Study Guide in Organic Chemistry’, VNU-HCM Publisher,
2013, Call No. 547.076 PH-N

Other references
[3] Paula Y. Bruice, ‘Organic chemistry’, 5th edition, Pearson Prentice Hall, 2007, Call No.
547 BR-P
[4] Graham T.W. Solomons, Craig B. Fryhle, ‘Organic chemistry’, 9th edition, John Wiley
& Sons, 2008, Call No. 547 SO-T
[5] John McMurry, ‘Fundamentals of Organic chemistry’, 7th edition, Pacific Grove,
CA : Brooks/Cole Pub. Co., 2011, Call No. 547 MC-J
[6] Janice Gorzynski Smith, “Organic Chemistry”, 2nd edition, McGraw-Hill, 2008,
Call No. 547 SM-J
[7] Harold Hart, Christopher M. Hadad, Leslie E. Craine, David J. Hart, "Organic
2
Chemistry: A Short Course", 13th edition, Cengage, 2011, Call No. 547 Org
 COURSE OUTLINE
• Isomerism
• Electronic & steric effects
• Common reaction mechanisms
• Alkanes
• Alkenes
• Alkadienes
• Alkynes
• Aromatic hydrocarbons
• Alkyl halides
• Alcohols & phenols
• Aldehydes & ketones
• Carboxylic acids
• Amines & diazoniums 3
 Chapter 1: ISOMERISM
Isomers: Compounds with the same molecular formula
but different structural formulas
Isomers

Constitutional isomers Stereoisomers

Conformational isomers Configurational isomers

Optical isomers /Enantiomers &

Geometric isomers
Diastereoisomers
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 CONSTITUTIONAL ISOMERS
Different compounds that have the same molecular
formula – but differ in their connectivity

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 STEREOISOMERS
Isomers that differ in the way their atoms
are arranged in space
Conformational isomers Configurational isomers

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 CONFORMATIONAL ISOMERS
• Different shapes of the same molecule resulting
from rotation around a single C-C bond
• Conformational isomers are not different
compounds

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Conformations of butane

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Exercise
Determine structures for the most stable conformations and
the least stable conformations of following compounds and
draw Newman projection of the bond marked in bracket, in
which the carbon with lower number is at the front:
 Least
stable

Most
stable
 Least
stable

Most
stable
 Least
stable

Most
stable
 Least
stable

Most
stable
Conformations of cyclohexane

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12
18
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With substituted cyclohexane, generally, the conformer having bulky
substituents at equatorial positions, more substituents at equatorial
positions, less interaction between substituents at axial positions
is more stable
Exercise

Determine the structure for the most stable

conformation of:
(i) trans-1-isopropyl-3-methylcyclohexane
(ii) cis-1,1,3,4-tetramethylcyclohexane
trans-1-isopropyl-3-methylcyclohexane

cis-1,1,3,4-tetramethylcyclohexane
 GEOMETRIC ISOMERS

There is no rotation around the C=C bond 23

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The E,Z system of nomenclature

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Cahn-Ingold-Prelog priority rules

Rule 1

Rule 2

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Rule 3

Rule 4

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 Exercise

Compare prioritiy of following groups based on

Cahn-Ingold-Prelog priority rules:

(a)

(b)
Prioritiy based on Cahn-Ingold-Prelog priority rules:

(a)

(b)
Exercise
What is the configuration (E or Z) of the following alkene?

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Exercise
What is the configuration (E or Z) of the following alkene?

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higher priority

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E,Z system vs. cis,trans system

cis isomer trans isomer

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Exercise
Determine all geometric isomers of following
compounds based on E-Z and cis-trans (if any):
(cis) (trans)
(Z) (E)
(2Z,6Z) (2Z,6E)

(2E,6Z) (2E,6E)
(E) (Z)
 OPTICAL ISOMERS
A chiral object

Nonsuperimposable
mirror image

An achiral object
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 OPTICAL ISOMERS
Optical isomers are configurational isomers
which are able to rotate plane-polarized light
clockwise or anticlockwise

plane-polarized light

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Optically inactive

Optically active

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 Asymmetric carbon
An asymmetric carbon is a carbon atom that is
bonded to 4 different groups

Optically active
(chiral)

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Exercise
Is there any asymmetric carbon in following compounds?
Exercise
Is there any asymmetric carbon in following compounds?

2 asymmetric
carbon
NOT
asymmetric
carbon

2 asymmetric 3 asymmetric
carbon carbon
Isomers with one asymmetric carbon

Nonsuperimposable mirror-image molecules are

called enantiomers 24
 Drawing enantiomers
Using perspective formulas:

• 2 bonds in the paper plane

Convention • 1 bond as a solid wedge
• 1 bond as a hatched wedge 25
 Drawing enantiomers
Using Fisher Projection formulas:

• Carbon chain is drawn along the

vertical line
Convention • Vertical lines: bonds going into
the page
• Horizontal lines: bonds coming
out of the page 26
Exercise

Convert following perspective projection to Fisher projection:

 NAMING ENANTIOMERS
RELATIVE CONFIGURATION: D-L SYSTEM

Glyceraldehyde: the standard compound for

chemical correlation of configuration

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D-L system is only useful for naming sugars &
aminoacids

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 NAMING ENANTIOMERS
ABSOLUTE CONFIGURATION: R-S SYSTEM
• Using Cahn-Ingold-Prelog
rules
• View the molecule with the
Convention
lowest priority group
for
pointing away
perspective
formulas • If the direction from highest
priority group to the next is
clockwise: R
• If the direction is
anticlockwise:S
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Exercise
In following structures, which one presents the enantiomer of
(R)-2-chlorobutane, which one is just a different presentation
of (R)-2-chlorobutane?
The enantiomer of (R)-2-chlorobutane: (A), (D), (G), (J), (K).
The different presentation of (R)-2-chlorobutane: (B), (C), (H), (I), (L), (M), (N), (O).
NOT the isomer of (R)-2-chlorobutane: (E), (F).
 • Using Cahn-Ingold-Prelog
rules
• When the lowest priority
group is on a vertical bond:
+ If the direction from highest
Convention priority group to the next is
for Fisher clockwise: R
Projection
+ If the direction is
formulas
anticlockwise:S
• When the lowest priority
group is on a horizontal bond:
+ opposite answers
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Exercise
In following structures, which one presents the enantiomer of
(S)-2-butanol, which one is just a different presentation of
(S)-2-butanol?
The enantiomer of (S)-2-butanol: (B), (C), (D), (E), (F), (G).
The different presentation of (S)-2-butanol: (A), (H), (I), (J), (L), (M), (N), (O), (Q),
(R), (S), (T).
NOT the isomer of (S)-2-butanol: (K), (P), (U).
Exercise
In following pairs of structures, which pair
presents a pair of enantiomers, which pair is just
different presentations of a compound?
two presentations of the same compound
present a pair of enantiomers

two presentations of the same compound

two presentations of the same compound present a pair of enantiomers

Isomers with more than one
asymmetric carbon

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Exercise

Determine the configuration of following

compounds based on R-S nomenclature
Exercise

Determine all optical isomers of 1-bromo-3-

chlorocyclohexane based on R-S
nomenclature (cyclohexane ring is not required
to present in the chair conformation)
Meso compounds

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Exercise
Determine absolute configurations of all
stereoisomers of following compounds in
perspective and Fisher projection:
meso enantiomers
enantiomers 1 enantiomers 2 enantiomers 3 enantiomers 4
pseudoasymmetric carbon

meso 1 meso 2 enantiomers

enantiomers 1

enantiomers 2
meso enantiomers
NO optical isomer, only cis-trans isomers
 Enantiomers vs diastereoisomers

• Enantiomers: Nonsuperimposable mirror images

• Diastereoisomers: not mirror images of each other
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Exercise

Draw enantiomer and diastereoisomers of

following compounds:
 ers
om
re oi s
ste
dia
rs
me
t io
an
en
 ers
om
re oi s
ste
dia
rs
me
t io
an
en
 Enantiomers vs diastereoisomers

• Enantiomers normally have identical physical &

chemical properties
• Enantiomers normally interact differently with
other chiral molecules
• Diastereoisomers can have different physical &
chemical properties
• Enantiomers are always chiral
• Diastereoisomers can be chiral or achiral (meso
compounds)

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 Separating enantiomers

Racemic mixture:
1/1 mixture of 2
enantiomers
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Read exercise 1.21, 1.22 và 1.23 to know
more about “enatiomeric excess”
CHIRALITY & BIOLOGICAL ACTIVITY

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CHIRALITY & BIOLOGICAL ACTIVITY

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