The most common

chemical
transformation of a
carbon-carbon double
bond.
addition reaction
A majority of addition
reactions are _______
due to the fact that the
C-C pi-bond is
relatively weak.
exothermic
 By convention,
exothermic reactions
have a _________ heat
of reaction.
negative
 Strong __________ such as HCl, HBr,
HI & H2SO4, rapidly add to the C=C
functional group of alkenes
to give products in which new covalent
bonds are formed to hydrogen and to
the conjugate base of
the acid.
Brønsted acids
 When addition reactions to
unsymmetrical alkenes are carried out,
one of the two possible constitutionally
isomeric products is formed
preferentially. Selectivity of this sort is
termed ________.
regioselectivity
The pKa of water is
about
5.7
The pKa of acid is
about
4.75
 A base induced by
intramolecular substitution
reaction forms a three-
membered cyclic ether
called a(n)
epoxide
Addition of hydrogen
to a carbon-carbon
double bond is called
Hydrogenation
 This rule states, "When a
compound HX is added to an
unsymmetrical alkene, the
hydrogen
becomes attached to the carbon
with the most hydrogens attached
to it already."
Markovnikov's Rule
 Which among the
following product is
formed when ethyne
undergoes
hydrogenation?
Acetaldehyde
Which of the following
is not a strong Brønsted
acid?
H2O
What is the unexpected
product of adding HCl
to 3,3-dimethyl-1-
butene?
 2-chloro-2,3-
dimethylbutane
 What is the expected
Markovnikov product of
adding HCl to 3,3-
dimethyl-1-butene?
 3-chloro-2,2-
dimethylbutane
 The halogens ______ and _______
add rapidly to a wide variety of
alkenes without inducing the kinds
of structural rearrangements noted for
strong acids
Cl, Br
By adding ______, the concentration
of HOCl can be greatly increased,
and the chlorohydrin
addition product obtained from
alkenes.
silver hydroxide
What does syn-addition
mean?
 The addition reactions
may bond from the same
side.
What does anti-addition
mean?
 The addition reactions
may bond from opposite
sides.
CHAPTER 9
 Alkyl halides are
organic molecules
containing a halogen
true
 Bulky group means
that the solvent is not a
good source of protons
false
 Halide ions must be
electron-withdrawing
to create a partial
positive on the carbon.
true
 Nucleophile aprotic
solvent is not required
for this reaction.
false
A polar just knocks off
the halogen and takes
its place
false
Backside attack leads
to inversion of
configuration
true
 Aprotic decrease
nucleophile strength
false
With substitution, your
nucleophile comes in
and takes the place of
the leaving group.
true
 The rate will be faster
with more suitable
substrates so an SN2 on
a methyl will go faster
than on
a 2°.
true
Elimination is a better leaving
group than t-butoxide because
the butoxide is so large that it
has
difficulty getting to the site of
reactivity.
false
Nucleophiles given will all be
negatively-charged, though
ammonia and amines are also
strong
nucleophiles
true
 The acetonitrile is
aprotic solvent is not
required for this
reaction.
false
Rearrangements will only occur
when the resulting carbocation is
more stable than the initial
carbocation.
true
The nucleophile often a polar,
protic solvent attaches to the
positively-charged carbon.
true
Substitution always has
the rearranged product.
true
It is also called 2-propanone or
dimethyl ketone, an organic
solvent of industrial and
chemical
significance.
Acetone
 An organosulfur
compound with the
formula (CH3)2SO.
Dimethyl Sulfoxide
 Often abbreviated
MeCN, is the chemical
compound with the
formula CH3CN
Acetonitrile
An organic compound
with the formula
(CH3)2NCH and
commonly abbreviated
as DMF.
Dimethylformamide
Described as when there
is a quaternary position
next to the initial
carbocation.
Alkyl Shift
CHAPTER 1O
The contributing conformations
average out to an achiral
conformation, then the molecule
is considered achiral.
true
 The fact that a 2-
dimensional formula is
given does not imply
that there are chiral
centers.
false
 If two or more of the atoms
directly attached to the chiral
center are of the same type,
look at the next atom to break
the tie.
true
It is important to emphasize that in trying to
break ties, one looks at the atoms directly
attached
to the element under observation before
looking at any others.
true
 Its chirality is strictly
due to a conformational
effect.
true
 When duplicating the atoms
involved in double or triple bonding
they are also being crossed over
at the same time.
true
 When the formula is
given to us in this way,
it’s easy to assign
configuration.
true
 The fact that a 3-D
representation is given
does not necessarily
mean there is a carbon
in the
molecule.
false
 It most common situations of this
type involve molecules which are
locked up into a chiral conformation
due to steric interactions that impede
free rotation around achiral.
false
 The molecule is locked
up in a conformation that
has no symmetry,
therefore it is chiral.
true
 Stereoisomers cannot
be converted into each
other without breaking
bonds.
true
It is the most common
type encountered in
this course will be the
molecule chiral.
false
A racemic mixture exhibits no
optical activity because the
activities of the individual
enantiomers
are equal.
true
If a mixture contains 75%
of one enantiomer and
25% of the other, the
optical purity is 75-25 =
50%.
true
Absolute and relative
configurations may or
may not coincide.
false
An important branch
of stereochemistry is
the study of chiral
molecules.
true
Stereoisomers compounds and
their mirror images are not
stereoisomers, since they are
identical.
false
Some achiral molecules
have chiral
conformations.
true
Racemic mixture is
super passable with
their mirror images
false
 The presence of one
chiral center renders
the entire molecule
chiral.
true
❖ Stereoisomers - Compounds that have the same molecular formula and the same
connectivity, but different arrangement of the atoms in 3-dimensional space. Stereoisomers
cannot be converted into each other without breaking bonds.
❖ Enantiomers – non-super passable mirror images or chiral molecules which are mirror
images.
❖ Chiral, or asymmetric carbon - A tetrahedral carbon atom bearing four different
substituents.
❖ Chirality centers, or stereocenters - Asymmetrically substituted atoms in a molecular
structure. The most common type encountered in this course will be the chiral carbon
described above.
❖ Diastereomers - Stereoisomers which are not enantiomers (or mirror images).
❖ Meso compounds, or meso forms - Symmetric, or achiral molecules that contain
stereocenters. Meso compounds and their mirror images are not stereoisomers, since they
are identical.
❖ Optical activity - The ability of chiral substances to rotate the plane of polarized light
by a specific angle.
❖ Dextrorotatory - Ability of chiral substances to rotate the plane of polarized light to the
right.
Levorotatory - Ability of chiral substances to rotate the plane of polarized light to the left.
❖ Specific rotation - The measured angle of rotation of polarized light by a pure chiral
sample under specified standard conditions (refer to textbook for a description of these).
❖ Racemic mixture, racemic modification, or racemate - A mixture consisting of equal
amounts of enantiomers. A racemic mixture exhibits no optical activity because the
activities of the individual enantiomers are equal and opposite in value, thereby canceling
each other out.
❖ Optical purity - The difference in percent between two enantiomers present in a
mixture in unequal amounts. For example, if a mixture contains 75% of one enantiomer and
25% of the other, the optical purity is 75-25 = 50%.
❖ Absolute configuration - A description of the precise 3-dimensional topography of the
molecule.
❖ Relative configuration - A description of the 3-dimensional topography of the
molecule relative to an arbitrary standard. Absolute and relative configurations may or may
not coincide.