the number of p+; mass number is the
sum of p+and n.Isotopes have the same
number of p+with different numbers of n.
The atomic weight of an element is the
average weighted mass of its atoms (1.1).
2. An atomicorbital (s, p, d, f) is the volume
of space around a nucleus where an
electron is most likely to be found. An
electron goes into the lowest energy
orbital available (aufbau principle), with
4.Lewis structures represent compounds,
showing all bonding and lone pair
The formal charge on an
number of valence minus 1/2 the
carbon;c a r ba n i o n s have a negatively
charged carbon; a carbonradical has a
carbon with an unpaired
atomic orbital has a radial node. There are three degenerate, perpendicularp orbitals; each has a node at its nucleus (1.5).
the energy required to break a bond.
Two atomic orbitals combine to form
two molecular orbitals, a bonding MO
120\u00b0 bond angles. Ethyne (with a triple
bond) hassp carbons and 180\u00b0 bond
bonds. The mores character, the
shorter and stronger the bond and the
larger the bond angle. (1.6\u20131.9, 1.14).
When atoms are the same size, the more electronegative the atom to which the hydrogen is attached, the stronger the acid. Relative electroneg- ativities:
are very different in size, the strongest
acid will have its hydrogen attached to
the largest atom. For example, acid
stronger the acid, the weaker its
conjugate base. Weak bases are stable
bases. ALewis acid accepts a share in a
show electron flow; the arrow begins
where the electrons originate and points
to where they end up (1.16\u20131.26).
single bonds. Constitutional isomers
have the same molecular formula but
differ in the way the atoms are connected.
that puts the lowest number in the name
of the compound. Substituents are listed
alphabetically; di, tri, tetra, are used for
identical alkyl groups, but are not
alphabetized;sec andtert are also not
alphabetized, but iso and cyclo are. In a
are named using a functional group suffix.
Substituents on the nitrogen are preceded
by anN. If a parent chain has a substituent,
the substituent gets the lowest number; if
it has a functional group, the functional
group gets the lowest number; if it has
both a substituent and a functional group,
the functional group gets the lowest
number. Only if the functional group gets
the same number in either direction, is the
adds to ansp2
carbon of the
adds to the
3. Alkyl halides and alcohols are 1\u00b0, 2\u00b0, or 3\u00b0
depending on whether the X or OH is on
a 1\u00b0, 2\u00b0, or 3\u00b0 carbon. Amines are 1\u00b0, 2\u00b0, or
3\u00b0 depending on how many alkyl groups
are bonded to N (2.4, 2.6, 2.7).
4. The stronger the intramolecular forces
holding molecules together, the higher
theboiling point: hydrogen bonds are
stronger thandipole-dipole interactions,
which are stronger than van der Waals
forces, which increase with molecular
weight and decrease with branching (2.9).
5. Polar compounds dissolve in polar
solvents; nonpolar compounds dissolve
in nonpolar solvents. An oxygen can drag
about 3 carbons into water (2.9).
causes one chair conformer to convert into
another chair conformer; bonds that are
axial in one are equatorial in the other. A
substituent is more stable in an equatorial
position. A cis isomer has substituents on
the same side of the ring; a trans isomer
has them on opposite sides (2.10\u20132.14).
carbons of an alkene and the four
atoms attached to them are in a plane.Cis
isomers have the hydrogens on the same
side of the double bond; intrans isomers
they are on opposite sides. TheE isomer
has the high priority groups (based on
atomic numbers) on opposite sides of the
double bond; theZ isomer has them on
the same side. Proceeding down a
substituent breaks a tie (3.5).
and the bond is anucleophile; the
carbocation is anelectrophile and
1. Hydrogen halides add to alkenes to form alkyl halides.Carbocations are stabilized byhyperconjugation( delocalization by overlap of adjacent bond orbitals
carbon bonded to the greater
number of hydrogens in order to form
the more stable carbocation (4.4).
3. The addition of water or an alcohol to an
alkene requires an acid catalyst. Addition
of water forms an alcohol; addition of an
alcohol forms an ether (4.5).
the intermediate in these reactions is not a
carbocation, carbocation rearrangements
cannot occur (4.7).
respectively. Carbocations are not formed
as intermediates, so carbocation
rearrangements do not occur (4.8).
to formepoxides. The reaction
isconcerted (it does not have an
to form an
alcohol. Borane is the electrophile that
adds to the less substituted
Alkenes: An Introduction to
Reactivity. Thermodynamics and
1.Alkenes are hydrocarbons with a double
bond. The total number of bonds and
rings is the degree of unsaturation. The
general molecular formula for a
hydrogens for each degree of
unsaturation. The parent hydrocabon is
the longest carbon chain that contains the
double bond, numbered so that the start
of the double bond is given the lowest
possible number.Alkadiene is used for
two double bonds. Vinylic carbons are
double-bonded carbons; allylic carbons
are adjacent to vinylic carbons (3.1\u20133.2).
has partially broken and partially formed
bonds; anintermediate has fully formed
bonds. The more stable the species, the
lower its energy. The change in Gibbs free
is related to the
equilibrium constant by
The formation of products with stronger
bonds and greater freedom of movement
If a system at
equilibrium is disturbed, it will adjust to
offset the disturbance (Le Chatlelier\u2019s
the highest point on the reaction
coordinate. The rate of a reaction is
directly proportional to a rate constant,k;
the smaller the rate constant, the slower
the reaction. The Arrhenius equation
relates the rate constant to the activation
9. Alkenes undergo catalytic (Pd/C, Pt/C,
Ni)hydrogenation to form alkanes. The
most stable alkene has the smallest heat of
atoms are arranged in space. Cis-trans isomers have either a double bond or a cyclic structure (5.1).
2. A molecule ischiral if it is
nonsuperimposable on its mirror image.
A carbon bonded to four different
substituents is an asymmetric center.
A molecule with one asymmetric center is
chiral; it can exist as a pair of
7. In a stereoselective reaction, one
stereoisomer is formed in preference to
another. In a stereospecific reaction,
stereoisomeric (e.g., cis and trans)
reactants form different stereoisomers as
products. When a reactant without an
asymmetric center forms a product with
one asymmetric center, the product will
be a racemic mixture. Electrophilic
addition reactions that form carbocation
intermediates involvesyn andanti
and hydroboration are syn additions; halogenation is an anti addition. CIS- SYN-ERYTHRO or -CIS (5.18, 5.19).
8.Enzymes andreceptors can distinguish
between enantiomers. Enzyme-catalyzed
reactions are completely stereoselective\u2014
only one stereoisomer is formed.
Enzyme-catalyzed reactions are
stereospecific\u2014the enzyme reacts with
only one stereoisomer (5.20, 5.21).
bond. Aterminal alkyne has the triple
bond at the end of a chain; otherwise, it is
an internal alkyne. A compound with a
double and a triple bond is named as an
4. Borane adds to an alkyne to form a vinyl-
borane, which is oxidized to an enol. An
internal alkyne tautomerizes to aketone: a
terminal alkyne requires disiamylborane
and forms analdehyde (6.8).
are shared by three or
more atoms. Benzene has delocalized
3. TheR,Ssystem is used to name chiral
compounds by prioritizing the four
substituents attached to the asymmetric
center based on atomic number. When the
lowest priority substituent points to the
rear, an arrow starting at the highest
priority substituent and pointing at the
second highest priority substituent is
clockwise if the compound has theR
configuration, and counterclockwise if it
has theS configuration (5.7).
those that rotate it to
the left arelevorotatory
Apolarimeter measures observed
5. Stereoisomers that are not mirror images
arediastereomers. Unlike enantiomers,
diastereomers possess different physical
and chemical properties. In compounds
with two asymmetric centers, the
configuration of one of the asymmetric
centers is the same in both diastereomers,
and the configuration of the other is not
the same in both. Compounds with two or
more asymmetric centers that possess a
5. Catalytic hydrogenation of an alkyne
forms an alkane. With Lindlar
catalyst, a cis alkene is formed; with
contributor has the same net charge. The
greater the predicted stability of the
resonance contributor, the more it
contributes to the hybrid. Destabilizing
features: incomplete octet, positively
charged electronegative atom, charge
separation (7.4, 7.5).
The greater the number of
relatively stable resonance contributors,
the greater the delocalization energy.
(LCAO). Two are placed in each MO,
starting from the lowest energy MO. The
number of MOs equals the number of
AOs; a node is added for each ascending
MO. The highest occupied MO (HOMO)
is the highest energy MO that contains
due to an
increase in delocalization energy upon
losing a proton (7.9).
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