Stereochemistry
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3/7/16
Stereochemistry
Single Jeopardy Answers
1. Isomer Types
Pts Answer
50
Compounds that have identical molecular
formulas but differ in the order in which the
atoms are connected.
100 Compounds that are connected in the same order
but differ in their spatial arrangement.
150 Compounds that are not the same but are mirror
images of each other.
200 Compounds that are stereoisomers but are not
mirror image.
250 A compound that contains more than one
stereocenter but is superimposable on it’s mirror
image.
2. Chirality
Pts Answer
50
The only unambiguous criteria for determining
chirality.
100
150
200
250
The general term for a carbon with four different
substituent groups attached to it.
This is the one test for chirality and relies only on
consideration of one structural representation of
the compound involved?
These are compounds that are superimposable on
their mirror image.
Molecules with ____ stereocenter(s) are always
chiral.
3. Optical Activity
Pts Answer
50
Compounds with the same molecular connectivity
but which rotate plane polarized light differently.
100 This is the type of light that is rotated differently
by optical isomers.
150 Enantiomers rotate light in ____ amounts but in
opposite directions.
200 Optical rotation can be used to determine
___________.
250 A mixture of optical isomers that exhibits no
optical activity is called a ____________.
2
Question
What are constitutional isomers?
What are stereoisomers?
What are enantiomers?
What are diastereomers?
What is a meso compound?
Question
What is the nonsuperimposable
nature of an object and its mirror
image?
What is a stereocenter?
What is the test for an internal plane
of symmetry?
What is achiral?
What is 1?
Question
What are optical isomers?
What is plane-polarized light?
What is equal?
What is the composition of the
mixture of enantiomers?
What is a racemic mixture?
Stereochemistry
4. Stereocenters
Pts Answer
50
These are the two designations for a stereocenter.
100 If present, this atom always has the lowest
priority when designating a stereocenter.
150 The direction that the substituents of an S
stereocenter are arranged in, when assigning
configuration.
200 If two atoms attached to a chiral center are
identical, to determine priority,
_________________ .
250 The names of the three scientists that developed
the system for naming stereocenters R or S.
5. Fischer
Pts Answer
50
The number of dimensions that a Fischer
projection depicts a tetrahedral carbon in.
100 These lines represent bonds directed towards the
viewer.
150 The number of degrees that a Fischer projection
can be rotated while retaining the spatial
arrangement of the original molecule.
200 Fischer projections are most “connected” with
this class of organic compounds?
250 If this is done an odd number of times to a Fischer
projection, the absolute configuration of the
molecule is changed.
6. n > 1
Pts Answer
50
The number of possible isomers based on the
number of stereocenters.
100 The possible combinations of types of
stereoisomers if there are 2 stereocenters.
150 Cis and trans isomers in cycloalkanes are ______.
200 The number of unique stereoisomers that can
result from a compound with a pair of
stereocenters bearing the same functional groups?
250 Disubstituted cyclic compounds can be meso
compounds if the ring substitutents have this
spatial arrangement.
3
Question
What is R or S?
What is hydrogen?
What is counter-clockwise?
What is step out until there is a
difference in the atoms in the
substituent group?
Who are Cahn, Ingold, and Prelog
Question
What is 2?
What are horizontal lines?
What is 180?
What are the sugars
(carbohydrates)?
What is switching any two
substituents?
Question
What is 2n?
What are R/R, R/S, S/R, and S/S?
What are diastereomers?
What is 3?
What is cis?
Stereochemistry
Double Jeopardy Answers
1. R or S
Pts Answer
100
H
Question
What is R?
Br
CH2CH3
200
CH3
H OH
What is R?
300
H
What is R?
HO2C
400
(H3C)3C
500
SH
CH3
CH3
What is S?
H
CH2CH2OCH2CH3
OH
HO
CH2NHCH3
H
HO
4
What is R?
Stereochemistry
2. n = ?
Pts Answer
100
Cl
Br
Question
What is 1?
H
F
200
O
H
HO
H
What is 3?
H
OH
H
OH
CH2OH
300
OH
HO
What is 1?
CH3
H3C
400
NH2
CH2OH
What is 2?
HO CH
O
HO
OH
500
What is 2?
O
5
Stereochemistry
3. Relationships
Pts Answer
100
CH
2F
H
200
CH3
H
H
H
Cl
Cl
What are enantiomers?
Cl
F
Cl
300
H
Cl
CH3
F
Cl
CH3
F
Question
What are constitutional isomers?
Cl
What are diastereomers?
Cl
400
H
CH3
Br
Cl
H
CH3
Cl
H
H
CH3
CH3
Br
H
Cl
CH3
H
Br
CH3
500
What are enantiomers?
CH3
H
Br
Cl
H
CH3
6
What are diastereomers?
Stereochemistry
4. # of Isomers
Pts Answer
100
CH
Question
What is 2?
3
F
Cl
H
H Cl
200
H3C
What is 4?
CH3
Br H
H Br
300
H3C
What is 3?
CH3
Br H
H Br H
400
H3C
500
What is 8?
CH3
Br H F
H3C
H
H
What is 3?
CH3
7
Stereochemistry
5. In Reactions
Pts Answer
100 The reason that the bromination of an alkane
results in a racemic product mixture.
200 If a reaction starts with achiral reagents, the
products have to overall be this.
300 A reaction that leads to the predominant
formation of one of several possible
stereoisomeric products is this.
400 In a chiral starting material, halogenation at the
stereocenter leads to this.
500 In a starting material with two stereocenters,
halogenation at one of the stereocenters results in
products formed in unequal proportions because
of this.
6. Chirality of every day objects
Pts Answer
100 A hand.
200 A spoon.
300 A baseball.
400 The earth.
500 An electric fan.
Question
What is the planar radical
intermediate?
What is achiral?
What is stereoselective?
What is a racemic mixture?
What is the difference in energy in
the transition states due to their
diastereomeric relationship?
Question
What is chiral?
What is achiral?
What is achiral?
What is chiral?
What is chiral? (fan blades are
always twisted)
8