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Exam 1 (Last year)
Arney
56
Organic Chemistry
Undergraduate 2
08/05/2014

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Term
An antibonding MO...
Definition
is higher in energy than the atomic orbitals it came from
Term
In a bond between B (boron) and C (carbon), the _____ atom is the negative end of the dipole
Definition
carbon
Term
The _________ arrow represents "donates 2 electrons to?"
Definition
upward curved
Term
On the periodic table, _________ and ____________ increases going to the left
Definition
Basicity
Nucleophilicity
Term
Molecules that have the same molecular formula but are not superimposable are
Definition
isomers
Term
Which atom(s) in a molecule of HSCH2CH2OH can act as (a) nucleophile(s)?
Definition
Sulfur and oxygen
Term
Given that dichloroacetic acid (Cl2CHCOOH) has a Ka = 1.8x10^-2 and acetic acid (CH3COOH) has a Ka = 1.8x10^-5, which acid is stronger?
Definition
Cl2CHCOOH
dichloroacetic acid
Term
In the equilibrium of two acids and their conjugate bases which side will be favored?
Definition
the side with the stronger acid
Term
Resonance structures are...
Definition
inadequate Lewis structures for molecules with delocalized electrons
Term
Lewis structures
Definition
-does not allow carbon to exceed an octet
-every pair of electrons may be on a single atom
-does not allow electron pairs to be shared by more than two atoms
Term
The hybridization of the C atom in C2H6 is
Definition
sp3
Term
One atomic mass number is defined as
Definition
a proton or a neutron in the nucleus
Term
The H-C-O bond angle in CH2O is approximately
Definition
120 degrees
Term
Pi orbitals are formed with _________ orbitals on adjacent atoms, sigma orbitals are formed with __________ orbitals, and unshared pairs of electrons reside in _______ orbitals
Definition
p; hybridized; hybridized
Term
4 electron domains
Definition
-tetrahedral geometry
-sp3 hybridization
-109.5 degree angles between electron domains
-4 hybridized orbitals
-0 remaining p-orbitals
-4 sigma orbitals possible
-0 pi orbitals possible
Term
3 electron domains
Definition
-trigonal planar geometry
-sp2 hybridization
-120 degree angles between electron domains
-3 hybridized orbitals
-1 remaining p-orbital
-3 sigma orbitals possible
-1 pi orbital possible
Term
2 electron domains
Definition
-linear geometry
-sp hybridization
-180 degree angles between electron domains
-2 hybridized orbitals
-2 remaining p-orbitals
-2 sigma orbitals possible
-2 pi orbitals possible
Term
Constitutional isomers
Definition
same molecular formula, but different connectivities
Term
Covalent bond
Definition
a shared pair of electrons
Term
Electronegativity
Definition
pull for shared electron pair
Term
Bronstead base
Definition
proton acceptor
Term
Resonance structures
Definition
structures of a molecule that only differ in pi electron and/or lone-pair placement
Term
Electrophile
Definition
electron pair acceptor
Term
Bonding MO
Definition
shared orbital that releases energy
Term
Lewis Theory
Definition
based on bond formation
Term
Sp2 hybrid orbitals
Definition
120 bond angles
Term
Double bond
Definition
composed of a sigma MO and a pi MO
Term
Valence electrons
Definition
outer shell electrons used to form bonds
Term
Acid
Definition
proton donor
Term
HO-
Definition
Arrhenius base
Term
Polar bond
Definition
unevenly shared pair of electrons
Term
Nonbonding
Definition
has about the same energy as initial atomic orbitals
Term
Molecular orbital
Definition
orbital shared by more than one atom
Term
Overlap
Definition
area of significant interaction between orbitals on different atoms
Term
Sp3 hybridization
Definition
109.5 degree bond angles, "tripod"
Term
Sigma MO
Definition
overlap along axis joining two nuclei
Term
Formal charge
Definition
electron counting on an atom
Term
Hybridization
Definition
recombining the atomic orbitals to give a new set
Term
Bronstead theory
Definition
based on the exchange of a proton "H+"
Term
Pi MO
Definition
overlap above & below the axis joining the nuclei
Term
Node
Definition
region of "0" (zero) electron density
Term
Linear
Definition
sp hybridized
Term
Enantiomers
Definition
mirror-image stereoisomers
Term
Stereoisomers
Definition
same connectivities, not superimposable
Term
Triple bond
Definition
has one sigma orbital and 2 pi orbitals
Term
Aromatic
Definition
has a benzene-type ring in its structure
Term
Degrees of Unsaturation
Definition
(# of rings) + (# of pi bonds)
Term
Allylic
Definition
adjacent to a C=C bond (C=C-C-X)
Term
Vinylic
Definition
attached to a C in a C=C bond (C=C-X)
Term
Electrophile
Definition
Lewis acid
Term
Dipole
Definition
separated regions of opposite charge
Term
Cyano group
Definition
component of nitriles
Term
Nucleophile
Definition
electron pair donor
Term
Carboxyl group
Definition
composed of a carbonyl attached to a hydroxyl
Term
Antibonding
Definition
higher in energy than original atomic orbitals
Term
Formyl group
Definition
composed of a carbonyl attached to a hydrogen
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