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 Isomers
Isomers: different compounds with the
same molecular formula
Constitutional isomers: isomers with a
different connectivity
Stereoisomers: isomers with the same
molecular formula, the same
connectivity but a different orientation
of their atoms in space that cannot be
interconverted by rotation about a single
bond

2
Isomerism → Constitutional
Isomers and Stereoisomers
Stereoisomers are isomers with the
same molecular formula and same
connectivity of atoms but different
arrangement of atoms in space

3
 Stereochemistry
is the chemistry of molecules in three
dimension

4
 Handedness
Stereochemistry of organic molecules
can be understood, if we understand the
meaning of handedness
the fundamental reason for this is that
our hands are not identical, rather they
are mirror images

5
 Chirality

The mirror image Objects which are chiral

of a chiral object is have a sense of
different and will not “handedness” and exist in
superimpose on the two forms.
original object.
6
The reason for Handedness→ chirality
• Although everything has a mirror image, mirror images
may or may not be superimposable.
• Some molecules are like hands. Left and right hands are
mirror images, but they are not identical, or
superimposable → chiral (property of handedness)

7
Mirror Image

8
 Chirality and
Nonchirality
Mirror image: the reflection of an object in a
mirror
Objects that are not superposable on their
mirror images are said to be chiral, that is,
they show handedness
Objects that are superposable on their mirror
images are said to be achiral, that is, they
do not show handedness. An achiral object
has at least one element of symmetry

9
 Achiral Molecules
• Do these molecules contain a Plane of Symmetry (Mirror Plane)?

10
 Chiral Molecules
• The molecule labeled A and its mirror image labeled B
are not superimposable. No matter how you rotate A and
B, all the atoms never align. Thus, CHBrClF is a chiral
molecule, and A and B are different compounds.
• A and B are stereoisomers—specifically, they are
enantiomers.
• A carbon atom with four different groups is a tetrahedral
stereogenic center.

11
 Chiral vs. Achiral
• With one stereogenic center, a molecule
will always be chiral.

• With two or more stereogenic centers, a

molecule may or may not be chiral, e.g.
Meso compound (contains a plane of
symmetry or a mirror plane)

12
 Chiral vs. Achiral
Chiral: from the Greek, cheir, hand
an object that is not superposable on its mirror image
Achiral: an object that lacks chirality; one that lacks
handedness
an achiral object has at least one element of symmetry
plane of symmetry: an imaginary plane passing through an
object dividing it so that one half is the mirror image of the
other half
center of symmetry: a point so situated that identical
components are located on opposite sides and equidistant
from that point along the axis passing through it

13
Elements of Symmetry
Symmetry in objects

14
Plane of Symmetry or Mirror plane

15
TWO VIEWS OF THE PLANE OF SYMMETRY

plane of
symmetry

F F

Cl Cl
Br Cl
Br
Cl
F side edge
Cl
Br view view
 Plane of Symmetry

Symmetry plane No symmetry plane

COOH CH3
H C H H C OH
COOH COOH

achiral chiral

17
Elements of Symmetry

Center of symmetry: a point so

situated that identical components of
the object are located equidistant on
opposite sides and equidistant from
the point along any axis passing
through the point
Br H

Cl
Cl

H Br center of  
symmetry
18
 Chiral Center
The most common (but not the only)
cause of chirality in organic
molecules is a tetrahedral atom,
most commonly carbon, bonded to
four different groups

A carbon with four different groups

bonded to it is called a chiral center
all chiral centers are stereocenters, but
not all stereocenters are chiral centers.

19
STEREOGENIC CARBON ATOMS
 Stereogenic Carbon
Atoms

Cl This is one type of ….

stereocenter
…. others are possible

H F
Br
A stereogenic carbon is tetrahedral and
has four different groups attached.
21
 Stereogenic Centers
• To locate a stereogenic center, examine the four groups
—not the four atoms—bonded to each tetrahedral
carbon atom in a molecule.
• Omit from consideration all C atoms that cannot be
tetrahedral stereogenic centers. These include
• Methylene and methyl units, i. e. CH2 and CH3 groups
respectively.
• Any sp or sp2 hybridized Carbons, e.g. triple bonds,
and double bonds in alkenes (C=C) and carbonyls
(C=O).

22
Enantiomers

23
 Enantiomers

One of a pair of molecular species that

are mirror images of each other and
not superposable.

They are mirror-image stereoisomers.

24
 Drawing Enantiomers
• To draw both enantiomers of a chiral compound such as
2-butanol, use the typical convention for depicting a
tetrahedron: place two bonds in the plane, one in front of
the plane on a wedge, and one behind the plane on a
dash. Then, to form the first enantiomer, arbitrarily place
the four groups—H, OH, CH3 and CH2CH3—on any bond
to the stereogenic center. Then draw the mirror image.

25
Pairs of Enantiomers

26
 Enantiomers

Cl Cl rotate

H F F
Br Br H

this molecule
is chiral
Cl
note that the fluorine
and bromine have been
interchanged in the

H Br enantiomer

F 27
 Enantiomers

HO O O OH
Lactic acid C C

C C
HO H H OH
CH3 H3 C

28
 Enantiomers
3-Chlorocyclohexene
Cl Cl

29
 Enantiomers
OH
CH3 CHCH2 OH
1,2-propanediol
OH OH

H3 C C CH2 OH HOH2 C C CH3

H H

30
 Enantiomers
A nitrogen chiral center

+ +
N N
H3 C CH2 CH3 CH3 CH2 CH3
A pair of enantiomers

31
Enantiomers
&
Diastereome
rs
32
 Enantiomers &
Diastereoisomer
Enantiomers: opposite
configurations at all stereogenic
centers.
Diastereomers: Stereoisomers that
are not mirror images of each
other. Different configuration at
some locations.

33
 Two Stereocenters
Cl Br Br Cl
d
H3C CH3 H3C CH3 i
a
H H H H s
t
entaiomers e
r
Cl Br Br Cl o
m
e
r
H3C H H CH3 s

H CH3 H3C H

entaiomers
34
 Enantiomers &
Diastereomers
For a molecule with 1 stereocenter, 2
stereoisomers are possible
For a molecule with 2 stereocenters, a
maximum of 4 stereoisomers are
possible
For a molecule with n stereocenters, a
maximum of 2n stereoisomers are
possible
2n-1 pairs of enantiomers

35
 Diastereomers
2,3,4-Trihydroxybutanal
two chiral centers
22 = 4 stereoisomers exist; two pairs of
enantiomers
CHO CHO CHO CHO
H C OH HO C H H C OH HO C H

H C OH HO C H HO C H H C OH

CH2 OH CH2 OH CH2 OH CH2 OH

A pair of enantiomers A pair of enantiomers
(Erythreose) (Threose)

Diastereomers:
stereoisomers that are not mirror images
refers to the relationship among two or more
objects 36
 Diastereomers
2,3-Dihydroxybutanedioic acid (tartaric
acid)
two chiral centers; 2n = 4, but only three
stereoisomers exist
COOH COOH COOH COOH

H C OH HO C H H C OH HO C H

H C OH HO C H HO C H H C OH

COOH COOH COOH COOH

A meso compound A pair of enantiomers
(plane of symmetry)

Meso compound: an achiral compound

possessing two or more chiral centers
that also has chiral isomers 37
 Diastereomers
2-Methylcyclopentanol

CH3 OH HO H3 C

H H H H
cis­ 2­Methylcyclopentanol
  (a pair of enantiomers) diastereomers

CH3 H H H3 C

H OH HO H
trans­ 2­Methylcyclopentanol
    (a pair of enantiomers)

38
 Diastereomers
1,2-Cyclopentanediol

OH HO OH HO

H H H H
cis- 1,2-Cyclopentanediol
(a meso compound)
diastereomers

OH H H HO

H HO OH H
trans- 1,2-Cyclopentanediol
(a pair of enantiomers)

39
 Diastereomers
cis-3-Methylcyclohexanol

H3 C OH HO CH3

40
 Diastereomers
trans-3-Methylcyclohexanol

H3 C CH3

OH HO

41
 Meso compounds

Meso compounds are achiral by virtue

of a symmetry plane, but contain a
stereogenic center.

plane of symmmetry mirror

Cl Cl Cl Cl

H3C CH3 H3C CH3

H H H H

42
 Meso compounds
Meso compound: achiral despite the
presence of stereogenic centers
Not optically active
Superposable on its mirror image
Has a plane of symmetry

43
The Three Stereoisomers of
2,3-dibromobutane

• Because one stereoisomer of 2,3-dibromobutane is

superimposable on its mirror image, there are only three
stereoisomers, not four.
44
 NUMBER OF
STEREOISOMERS POSSIBLE
 How Many Stereoisomers
Are Possible?

maximum number of stereoisomers

sometimes fewer = 2 n
,
than this number
will exist

where n = number of stereocenters

(sterogenic carbons)
 CH2OH OH RR
RS
CH3 *
C CH2 CH CH CH3 SR
* SS
CH3 CH3
22 = 4 stereoisomers
CH3
RRR RSS
* RRS SRS
RSR SSR
*
* OH SRR SSS

CH3 CH
CH3 23 = 8 stereoisomers
 CONFIGURATION

ABSOLUTE CONFIGURATION ( R / S )
 CONFIGURATION

The three dimensional arrangement of the

groups attached to an atom

Stereoisomers differ in the configuration at one or

more of their atoms.
 CONFIGURATION
→ R,S convention

1 2 2 counter
clockwise 1
clockwise
C C
4 4
3 3
view with
substituent
of lowest
priority in
back
R (rectus) S (sinister)
 Rules for Labeling Stereogenic Centers with R or S

• Since enantiomers are two different compounds, they

need to be distinguished by name. This is done by
adding the prefix R or S to the IUPAC name of the
enantiomer.
• Naming enantiomers with the prefixes R or S is called
the Cahn-Ingold-Prelog system.
• To designate enantiomers as R or S, priorities must be
assigned to each group bonded to the stereogenic
center, in order of decreasing atomic number. The atom
of highest atomic number gets the highest priority (1).

51
Priority Rules for Naming Enantiomers (R or S)

• If two atoms on a stereogenic center are the same,

assign priority based on the atomic number of the atoms
bonded to these atoms. One atom of higher priority
determines the higher priority.

52
Priority of Isotopes on a Stereogenic Center
• If two isotopes are bonded to the stereogenic center,
assign priorities in order of decreasing mass number.
Thus, in comparing the three isotopes of hydrogen, the
order of priorities is:

53
Priority Rules for Multiple Bonds in (R or S) Labeling
• To assign a priority to an atom that is part of a multiple bond,
treat a multiply bonded atom as an equivalent number of
singly bonded atoms. For example, the C of a C=O is
considered to be bonded to two O atoms.

• Other common multiple bonds are drawn below:

54
Examples Assigning Priorities

55
Cahn-Ingold-Prelog System
for Naming Enantiomers R
or S

56
R or S Enantiomers

57
Positioning the Molecule for R/S Assignment

58
R-enantiomer (Clockwise Rotation)
S-enantiomer (Counterclockwise Rotation)

59
Manipulation of Chiral Molecules

60
The molecule is rotated to put the
lowest priority group back
If the groups descend in priority (a,b then
c) in clockwise direction the enantiomer
is R
If the groups descend in priority in
counterclockwise direction the
enantiomer is S

61
 R,S Convention
Priority rules (Cahn, Ingold, Prelog)
Each atom bonded to the
stereocenter is assigned a priority,
based on atomic number. The higher
the atomic number, the higher the
1
priority
6 7 8 16 17 35 53
H CH3 NH2 OH SH Cl Br I

Increasing Priority

62
 R,S Convention
If priority cannot be assigned on the
basis of the atoms bonded to the
stereocenter, look to the next set of
atoms. Priority is assigned at the first
point of difference.
1 6 7 8
CH2 H CH2 CH3 CH2 NH2 CH2 OH

Increasing Priority

63
 R,S Convention
Atoms participating in a double or
triple bond are considered to be
bonded to an equivalent number of
similar atoms by single bonds
C C
is treated as
-CH=CH2 -CH-CH2

O O C
is treated as
-CH C O
H
C C
is treated as
C CH C C H
C C

64
 Priorities
1. -OH H
HO COOH
2. -COOH C
3. -CH3 CH3

4. -H (R)-(-)-lactic acid

H
HOOC OH
C
CH3

(S)-(+)-lactic acid 65
Bromochlorofluoroiodometha
ne
1 1
I I
4 4
F C C
2 F
Cl Br Br Cl
3 3
2

R S
Enantiomers 66
R and S Assignments in Compounds
with Two or More Stereogenic Centers.
• When a compound has more than one stereogenic
center, the R and S configuration must be assigned to
each of them.

One stereoisomer of 2,3-dibromopentane

The complete name is (2S,3R)-2,3-dibromopentane

67
Stereoisomerism of Cyclic
Compounds
1,4-dimethylcyclohexane
Neither the cis not trans isomers is optically
active
Each has a plane of symmetry

68
1,3-dimethylcyclohexane
The trans and cis compounds each have
two stereogenic centers
The cis compound has a plane of
symmetry and is meso
The trans compound exists as a pair of
enantiomers

69
 Properties of
Stereoisomers

70
 Properties of
Stereoisomers
Enantiomers have identical physical
and chemical properties in achiral
environments
Diastereomers are different
compounds and have different
physical and chemical properties
meso tartaric acid, for example, has
different physical and chemical properties
from its enantiomers (see Table 3.1)

71
Plane-Polarized Light

Ordinary light: light vibrating in all

planes perpendicular to its
direction of propagation
Plane-polarized light: light
vibrating only in parallel planes
Optically active: refers to a
compound that rotates the plane
of plane-polarized light

72
Plane-Polarized Light
plane-polarized light is the vector
sum of left and right circularly
polarized light
circularly polarized light reacts one
way with an R chiral center, and the
opposite way with its enantiomer
the result of interaction of plane-
polarized light with a chiral compound
is rotation of the plane of polarization

73
Plane-Polarized Light

Polarimeter: a device for

measuring the extent of rotation of
plane-polarized light

74
 Optical Activity
observed rotation: the number of degrees, α ,
through which a compound rotates the plane
of polarized light
dextrorotatory (+): refers to a compound that
rotates the plane of polarized light to the right
levorotatory (-): refers to a compound that
rotates of the plane of polarized light to the
left
specific rotation: observed rotation when a
pure sample is placed in a tube 1.0 dm in
length and concentration in g/mL (density); for
a solution, concentration
COOH is expressed
COOH in g/ 100
mL C C
H H
H3 C OH CH3
HO
(S)­(+)­Lactic acid (R)­(­)­Lactatic acid
21 21
[α]D = +2.6° [α]D = ­2.6°

75
 Optical Purity
Optical purity: a way of describing the
composition of a mixture of enantiomers

[α ]sam ple
Percent optical purity = x 100
[α ]pure enantio mer
Enantiomeric excess: the difference between
the percentage of two enantiomers in a
mixture

[R] ­ [S]
Enantiomeric excess (ee) = x 100 = %R ­ %S
[R] + [S]
optical purity is numerically equal to enantiomeric
excess, but is experimentally determined

76
 Resolution

Racemic mixture: an equimolar

mixture of two enantiomers
because a racemic mixture contains
equal numbers of dextrorotatory and
levorotatory molecules, its specific
rotation is zero
Resolution: the separation of a
racemic mixture into its enantiomers

77
 Racemates
• An equal amount of two enantiomers is called a
racemate or a racemic mixture. A racemic mixture is
optically inactive. Because two enantiomers rotate
plane-polarized light to an equal extent but in opposite
directions, the rotations cancel, and no rotation is
observed.

78
 Specific Rotation
• Specific rotation is a standardized physical constant for
the amount that a chiral compound rotates plane-
polarized light. Specific rotation is denoted by the
symbol [α ] and defined using a specific sample tube
length (l, in dm), concentration (c in g/mL), temperature
(25 0C) and wavelength (589 nm).

79
 Discovery of
Enantiomers

“There is no
doubt that in - +
dextro tartaric
COO Na
acid there exists H C OH
an assymetric
arrangement HO C H
having a
nonsuperimposi - +
COO Na
ble image.”

80
 OH OH meso
HOOC COOH
H
Tartaric Acid
H

OH OH OH OH
HOOC H H COOH
H COOH HOOC H

(+)-tartaric acid (-)-tartaric acid

enantiomers

OH OH meso ALSO FOUND

(as a minor component)
HOOC COOH
H H [α ]D = 0
more about this
meso -tartaric acid compound later
OH OH OH OH 81
 Diastereoisomer
Stereoisomers
that are not
mirror images H
COOH
NH 2
COOH
H2N C H
of each other. C
Different C C
H OH H OH
configuration at CH 3 CH3
some locations.

82
 Diastereomers
Threonine: 2 pairs H
COOH
NH2 COOH
H 2N H
of enantiomers C C
C C
H OH HO H
CH3 H3C
2R,3R 2S,3S 2R,3S & 2S,3R 2R, 3R 2S, 3S
2S,3S 2R,3R 2R,3S & 2S,3R COOH COOH
2R,3S 2S,3R 2R,3R & 2S,3S H C NH2 H 2N C H
2S,3R 2R,3S 2R,3R & 2S,3S C C
HO H H OH
H3C CH3

2R, 3S 2S, 3R

83
 Enantiomers &
Diastereomers
For tartaric acid, the three possible
stereoisomers are one meso
compound and a pair of
enantiomers.

Meso compound: an achiral

compound possessing two or more
stereocenters.
84
 Symmetry Plane
2R, 3S and 2S, 3R COOH COOH
H C OH HO H
are identical C
C C
Molecule has a HO H H OH
COOH COOH
plane of 2R, 3R 2S, 3S
symmetry COOH COOH
perpendicular to H C OH HO
C
H

C-C and is C C
H OH
therefore achira COOH
HO H
COOH

2R, 3S 2S, 3R

85
 Symmetry Plane
2R, 3S and 2S, 3R are COOH COOH
identical H C OH HO H
C
Molecule has a plane C C
of symmetry HO H H OH
COOH COOH
perpendicular to C-C
2R, 3R 2S, 3S
and is therefore
achira COOH COOH
H C OH HO Mirror
H
One meso compound C
image is
and a pair of C
enantiomers H OH HO
identical
C
H
COOH COOH

2R, 3S 2S, 3R

86
 CH3CHCHCH3
Cl Br
2-Bromo-3-chlorobutane
mirror
Cl Br Br Cl
S R S R
CH3 CH3 CH3 CH3
H H H H
enantiomers 1
diastereomers
Cl Br Br Cl
S S R R
CH3 H H CH3
H CH3 CH3 H
enantiomers 2

87
 CH3CHCHCH3
Cl Cl
2,3-Dichlorobutane
Cl Cl Cl Cl
S R mirror image
CH3 CH3 CH3 is identical CH3
H H H H
meso
diastereomers
Cl Cl Cl Cl
S S R R
CH3 H H CH3
H CH3 CH3 H
enantiomers

88
 Tartaric Acid
(-) - tartaric acid (+) - tartaric acid
[α ]D = -12.0o [α ]D = +12.0o
mp 168 - 170o mp 168 - 170o
solubility of 1 g
solubility of 1 g
0.75 mL H2O
0.75 mL H2O
1.7 mL methanol
1.7 mL methanol 250 mL ether
250 mL ether insoluble CHCl3
insoluble CHCl3 d = 1.758 g/mL
d = 1.758 g/mL

meso - tartaric acid

[α ]D = 0o solubility of 1 g
mp 140o 0.94 mL
H 2O 89
 Fischer
Projections

90
 CH3

H OH

Fischer Projections CH2 CH3

Fischer projection: a two-dimensional

representation showing the
configuration of a stereocenter
horizontal lines represent bonds
projecting forward
vertical lines represent bonds projecting
to the rear
the only atom in the plane of the paper
is the stereocenter

91
Fischer Projections

COOH COOH
C H OH
H
OH CH3 CH3
How?
(R)-lactic acid
92
Fischer Projections

COOH COOH

H C H OH
OH CH3 CH3

93
 Fischer Projections

COOH COOH
H OH H OH
CH3 CH3
94
 Fischer Projections

1. Orient the stereocenter so that bonds

projecting away from you are vertical
and bonds projecting toward you are
horizontal
2. Flatten
OH it to two dimensions
CH CH 3 3

(1)
H C H C OH (2) H OH
CH3
CH3 CH2
CH2 CH3 CH2 CH3
(S)­2­Butanol       (S)­2­Butanol 
(3­D formula) (Fischer projection)

95
 Assigning R,S
Configuration
Lowest priority group goes to the
top.
View rest of projection.
A curved arrow from highest to
lowest priority groups.
Clockwise - R (rectus)
Counterclockwise - S (sinister)

96
 Assigning R,S
Configuration
4

H
2

3 H 3C COOH
OH
1 s-lactic acid
97
 Rules of Motion
 Can rotate 180°, but not 90°
because 90° disobeys the Fischer
projection.
Same groups go in and out of plane

COOH COOH CH3

CH 3
H OH 180 HO H
=H OH HO H =
CH3 CH3 COOH COOH

98
 Rules of Motion
 Can rotate 180°, but not 90° because
90° disobeys the Fischer projection.
Different groups go in and out of plane
This generates an enantiomeric structure

COOH COOH H
H
H OH 90 H3C COOH
=H OH H3C COOH =
CH3 CH3 OH OH

(R)-lactic acid (S)-lactic acid

99
 Rules of Motion
 One group can be held steady and
the others rotated.

COOH COOH
H OH same as HO CH3
CH3 H

100
 Rules of Motion
To determine if two Fischer
projections represent the same
enantiomer carry out allowed
motions.
H C 2H 5 OH
H 3C C 2H 5 HO H H CH3
OH CH3 C2H 5

A B C
101
 H C2H 5 OH
H 3C C2H 5 HO H H CH3
OH CH 3 C2H 5

Rules of Motion A B C

By performing two allowed

movements on B, we are able to
generate projection A. Therefore,
they are identical.
CH2CH 3 HO H
CH3 CH3CH2
HO H H CH2CH3 CH3 CH 2CH3
CH 3 CH 3 HO

B A

102
 H C2H 5 OH
H 3C C2H 5 HO H H CH3
OH CH 3 C2H 5

Rules of Motion A B C

Perform one of the two allowed

motions to place the group with
lowest priority at the top of the
Fischer projection.

OH CH 2CH3 H
H CH 3 180 H OH CH 3
H 3C CH 2CH
90
CH 2CH3 OH OH

C not A
103
 Priorities
HOOC
1. NH2 CH3
H
H 2N H HOOC NH2
2. COOH CH3 CH3
3. CH3
4. H
H H HOOC
HOOC NH2 HOOC NH2
CH3 CH3 H 2N H
CH3
S - stereochemistry 104
 1-Bromo-2-
chlorocyclohexane
Br Cl Cl Br cis

enantiomers
diastereomers

Br Br trans

Cl Cl
enantiomers
105
 1-Bromo-2-
chlorocyclopropane

Br R Cl Cl R Br
S S
cis

enantiomers
diastereomers
Br Br
R R S S
trans
Cl Cl

enantiomers
106
 1,2-Dibromocyclopropane
mirror image identical

Br Br Br Br
cis

meso
diastereomers

Br Br
trans
Br Br

enantiomers 107
 Biological Significance of
Stereoisomers

Structure causes Properties

Stereochemistry Biological effects

Example
•Pasteur’s plant mold metabolized (+)-tartaric acid but not (-)-tartaric acid

108
 Biological Significance of
Stereoisomers
Thalidomide
O
•Marketed in 50 countries 1956-1962
Sedative for “hysterical” pregnant women
N O
Antiemetic to combat morning sickness
N
•Caused thousands of birth defects
O O H

Teratogen: causes fetal

abnormalities One stereocenter

•Sold as racemic mixture: 1:1 mixture of enantiomers

R enantiomer = antiemetic (not teratogenic)
S enantiomer = teratogenic (not antiemetic)
•Single-enantiomer drug not useful: quickly racemizes in body

109
 Biological Significance of
Stereoisomers
Another Biological Effect: Odor
O O
enantiomers

H H

(R)-(-)-carvone (S)-(+)-carvone
smells like spearmint smells like caraway

Mirror image molecules do not have “mirror image effects”

110
 Biological Significance of
Stereoisomers
Of Hands, Gloves, and Biology
Why do stereoisomers have different biological properties?
•Many biological effects involve interaction with a cavity in enzyme or receptor
•Good fit to cavity (i.e., strong binding) triggers enzyme or receptor
R H

OH
•Enzymes and receptors are proteins; built from amino acids: H2N

O
•Most amino acids are chiral, so protein cavity is also chiral
•Metaphor: Stereoisomer = left hand or right hand
Protein hole = left glove or right glove
Left hand fits left glove but not right glove
Left hand triggers “left protein” but not “right protein”
•(R)-carvone triggers spearmint smell receptor but not caraway smell
receptor

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