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MCAT > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

1
Q

IUPAC Nomenclature Steps

A
  1. Identify longest chain containing highest order group
  2. Number the chain
  3. Name the substituents
  4. Assign a number to the substituents
  5. Complete the name
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2
Q

Substituent

A

any functional group not part of the parent chain

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3
Q

Alkanes

A

hydrocarbons without any double or triple bond; -ane

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4
Q

Alkenes

A

hydrocarbon with double bonds;-ene

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5
Q

Alkynes

A

hydrocarbon with triple bonds; -yne

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6
Q

Alcohols

A

contain hydroxyl group that substitues for one or more hydrogens in the chain; -ol;hydroxy-

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7
Q

Diols

A

alcohol with two hydroxyl groups

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8
Q

geminal diols

A

alcohol with two hydroxyls on the same carbon

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9
Q

Vicinal diol

A

alcohol with two hydroxyls on adjacent carbons

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10
Q

Aldehyde

A

contains a carbonyl on terminal carbon also attached to hydrogen; -al; oxo-

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11
Q

Ketones

A

carbonyl group on a nonterminal carbon; -one; oxo-; keto-

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12
Q

Carbonyl group

A

C=O; aldehydes and ketones

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13
Q

Carboxylic Acid

A

carbonyl and hydroxyl on same carbon (RCOOH); always terminal

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14
Q

Carboxylic Acid Derivatives

A

compound created from a carboxylic acid by a nucleophilic acyl substitution; anhydrides, esters, amides, etc.

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15
Q

Esters

A

carboxylic acid derivatives where -OH replaced with -OR; -oate; alkoxycarbonyl-

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16
Q

Amides

A

carboxylic acid derivates where -OH replaced with -RCONR2; -amide; carbamoyl-; amido-

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17
Q

Anhydrides

A

contains 2 carbonyls separated by an oxygen (RCOOCOR); condensation dimer of a carboxylic acid

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18
Q

Dimer

A

molecular complex with two identical molecules linked together

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19
Q

Structural Isomer

A

share molecular formula; different physical and chemical properties

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20
Q

Conformational Isomer

A

differ by rotation around single sigma bond

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21
Q

Staggered conformation

A

when a molecule has no overlapping substituents along the line of sight between two carbons, as seen in Newman projection

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22
Q

Newman Projection

A

A method of visualizing a compound in which the line of sight is down a carbon-carbon bond axis

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23
Q

anti-staggered molecules

A

the two largest groups are antiperiplanar to eachother; the most energetically favourable conformation

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24
Q

gauche staggered molecules

A

In which the two largest groups are 60 degrees apart

25
Eclipsed conformations
groups directly in front of eachother as seen in Newman Projection
26
totally eclipsed conformations
Two larger groups are directly in front of one another and strain is maximized
27
angle strain
Increased energy that results when bond angles deviate from their ideal values
28
torsional strain
from eclipsing conformations
29
nonbonded strain
from interactions between substituents attached to nonadjacent carbons
30
axial
describes groups on a cyclic molecule that are perpindicular to the plane of the molecule, pointing straight up or down
31
equatorial
describes groups on a cyclic molecule that are in the plane of the molecule
32
Substituent classification (cyclohexane)
axial, equatorial
33
Configurational isomers
Isomers that can only interconvert by breaking bonds;enatiomers, diasteriomers, cis-trans isomers
34
Enantiomers
mirror images of a chiral molecule; have the same chemical and physical properties
35
Racemic Mixture
A mixture where both (+) and (-) enantiomers are present in equal concentrations
36
Meso Compound
A molecule with chiral centres but is not optically active because it has an internal plane of symmetry
37
Diastereomers
Non-mirror image configurational isomers that differ at least one-but not all-chiral carbons; different chemical and physical compounds
38
Relative Configuration
The spatial arrangement of groups in a chiral molecule compared to another chiral molecule
39
Absolute Configuration
The exact spatial arrangement of atoms or groups in a chiral molecule; designated by R and S
40
Cahn-Ingold-Prelog priority rules
ASHLEY
41
Fischer diagrams
A system to represent three dimensional molecules using lines and wedges
42
Cis-trans isomers
Diastereomers with different arrangements of substituents around an immovable bond
43
Chiral Centres
Atoms that are chiral within a molecule
44
Chiral
a molecule or carbon atom bonded to four different groups and without a plane of symmetry; non-superimposable and has an enantiomer
45
Principal quantum number, n
describes the energy level in which an electron resides and indicates the distance from the nucleus to the electron; 1 to infinity
46
Azimuthal quantum number, l
determines the subshell in which an electron resides; 0 to n-1
47
Magnetic quantum number, ml
the orbital in which an electron resides; -1 to +1
48
Spin quantum number, ms
spin of an electron; +-0.5
49
Bonding Orbitals
A lower energy, more stable orbital that results from the overlap of wave functions with the same sign
50
Antibonding Orbitals
a higher energy, less stable orbital that results from the overlap of wave functions with opposite signs
51
Sigma bonds
single bonds
52
Pi bonds
sharing of electrons
53
Double bonds
one sigma and one pi bond
54
Triple bonds
one sigma and 2 pi bonds
55
sp3
hybrid orbital with 25% s and 75% p
56
sp2
hybrid with 33% s and 67% p
57
sp
hybrid with 50% s and 50% p
58
Resonance
Delocalization of pi electrons, which increase the stability of a molecule
59
Conjugation
Alternating single and multiple bonds to create a system of parallel, unhybridized p orbitals

MCAT (6 decks)

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