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MCAT > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

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MCAT 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
Q

Eclipsed conformations

A

groups directly in front of eachother as seen in Newman Projection

26
Q

totally eclipsed conformations

A

Two larger groups are directly in front of one another and strain is maximized

27
Q

angle strain

A

Increased energy that results when bond angles deviate from their ideal values

28
Q

torsional strain

A

from eclipsing conformations

29
Q

nonbonded strain

A

from interactions between substituents attached to nonadjacent carbons

30
Q

axial

A

describes groups on a cyclic molecule that are perpindicular to the plane of the molecule, pointing straight up or down

31
Q

equatorial

A

describes groups on a cyclic molecule that are in the plane of the molecule

32
Q

Substituent classification (cyclohexane)

A

axial, equatorial

33
Q

Configurational isomers

A

Isomers that can only interconvert by breaking bonds;enatiomers, diasteriomers, cis-trans isomers

34
Q

Enantiomers

A

mirror images of a chiral molecule; have the same chemical and physical properties

35
Q

Racemic Mixture

A

A mixture where both (+) and (-) enantiomers are present in equal concentrations

36
Q

Meso Compound

A

A molecule with chiral centres but is not optically active because it has an internal plane of symmetry

37
Q

Diastereomers

A

Non-mirror image configurational isomers that differ at least one-but not all-chiral carbons; different chemical and physical compounds

38
Q

Relative Configuration

A

The spatial arrangement of groups in a chiral molecule compared to another chiral molecule

39
Q

Absolute Configuration

A

The exact spatial arrangement of atoms or groups in a chiral molecule; designated by R and S

40
Q

Cahn-Ingold-Prelog priority rules

A

ASHLEY

41
Q

Fischer diagrams

A

A system to represent three dimensional molecules using lines and wedges

42
Q

Cis-trans isomers

A

Diastereomers with different arrangements of substituents around an immovable bond

43
Q

Chiral Centres

A

Atoms that are chiral within a molecule

44
Q

Chiral

A

a molecule or carbon atom bonded to four different groups and without a plane of symmetry; non-superimposable and has an enantiomer

45
Q

Principal quantum number, n

A

describes the energy level in which an electron resides and indicates the distance from the nucleus to the electron; 1 to infinity

46
Q

Azimuthal quantum number, l

A

determines the subshell in which an electron resides; 0 to n-1

47
Q

Magnetic quantum number, ml

A

the orbital in which an electron resides; -1 to +1

48
Q

Spin quantum number, ms

A

spin of an electron; +-0.5

49
Q

Bonding Orbitals

A

A lower energy, more stable orbital that results from the overlap of wave functions with the same sign

50
Q

Antibonding Orbitals

A

a higher energy, less stable orbital that results from the overlap of wave functions with opposite signs

51
Q

Sigma bonds

A

single bonds

52
Q

Pi bonds

A

sharing of electrons

53
Q

Double bonds

A

one sigma and one pi bond

54
Q

Triple bonds

A

one sigma and 2 pi bonds

55
Q

sp3

A

hybrid orbital with 25% s and 75% p

56
Q

sp2

A

hybrid with 33% s and 67% p

57
Q

sp

A

hybrid with 50% s and 50% p

58
Q

Resonance

A

Delocalization of pi electrons, which increase the stability of a molecule

59
Q

Conjugation

A

Alternating single and multiple bonds to create a system of parallel, unhybridized p orbitals

MCAT (6 decks)

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