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MCAT > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

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MCAT flashcards
1
Q

Geminal diols

A

Diols with hydroxyl groups on the same carbon

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2
Q

Vicinal diols

A

Diols with hydroxyl groups on adjacent carbons

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3
Q

Methanal common name

A

Formaldehyde

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4
Q

Ethanal common name

A

Acetaldehyde

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5
Q

Propanal common name

A

Propionaldehyde

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6
Q

3C ketone common name

A

Acetone

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7
Q

Priority of substituents

A

Carboxylic acid > anhydride > ester > amide > aldehyde > ketone > alcohol > alkene ≥ alkyne > alkane

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8
Q

Porphyrin

A

The structure that makes up heme. It is made up of pyrrole rings (5 membered ring with a N)

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9
Q

Constitutional isomers

A

Also called structural isomers. Structures with similar molecular formulas, but different physical and chemical properties

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10
Q

Stereoisomers

A

Structures with the same chemical formula and connectivity, but differ in orientation

*A molecule with n chiral centers will have 2ⁿ stereoisomers

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11
Q

Conformational isomers

A

Structures that differ in rotation around sigma bonds. Varying degrees of rotation around single bonds creates different levels of strain

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12
Q

Angle strain

A

Strain caused when the molecule is stretched or compressed. Bond angles are not ideal.

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13
Q

Torsinal strain

A

Strain caused by gauche or eclipsed interactions

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14
Q

Non-bonded strain

A

Strain caused by non-adjacent atoms competing for space

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15
Q

Axial position

A

Perpendicular to the plane (sticking up or down)

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16
Q

Equitorial position

A

Parallel to the plane (sticking out)

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17
Q

Relative configuration

A

relationship of the configuration of one chiral molecule to another. Ex/ Cis, Trans, E/Z

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18
Q

Absolute configuration

A

exact spatial arrangement of the atoms or groups on a chiral molecule. Ex/ R/S

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19
Q

Chiral molecule

A

mirror image of a molecule can not be superimposed (4 different substituents)

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20
Q

Achiral molecule

A

mirror image can be superimposed (only 3 different substituents)

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21
Q

Dextrorotatory (d)

A

(+) rotating to the right

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22
Q

Levorotatory (l)

A

(-) rotating to the left

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23
Q

Specific rotation

A

The change in orientation of plane polarized light as it passes through a sample of a cmpd. This does not have to do with D and L configurations, only (+) and (-)

[α] = α[observed] / c x l
c = concentration in g/mL
l = length of path in dm (deci = 10⁻¹)
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24
Q

Racemic mixture

A

When both (+) and (-) enantiomers are present in equal concentrations. *The rotations cancel each other out and there is no optical activity

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25
Q

Diastereomer

A

Non-mirror image configurational isomers. They are molecules with at least 2 chiral center and differ at some but not all of them

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26
Q

Cis-tras (geometric) isomers

A

Type of diastereomer where the substituents differ in their position around an immovable bond. Cis is same side, trans is opposite

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27
Q

Meso compounds

A

Molecules with chiral centers but contain an internal plane of symmetry (optically inactive). They are super imposable mirror images

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28
Q

E and Z form

A

Used to describe compounds with polysubstituted double bonds. Priority of substituents has to be assigned on each side of the bond (L and R). Then the E and Z designations are assigned if these highest priority substituents are on the same side or opposite sides of the bond (top or bottom)

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29
Q

Fischer projection

A

Horizontal lines indicate bonds that project out of the page (wedges). Vertical lines indicate bonds that project into the page (dashes)

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30
Q

Hybridization

A

describes how bonds with different energy orbitals make up the same type of bond

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31
Q

Hybrid orbital theory

A

In order for a molecule to form equal bonds, electrons occupy hybrid orbitals that are formed from pre-existing orbitals

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32
Q

Derivative

A

a compound that can be imagined to arise, or actually be synthesized, from a parent compound by replacement of one atom with another atom or group of atoms

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33
Q

Acid dissociation constant

A

Ka = [H+][A-] / [HA]
pKa = -log(Ka)
The more acidic a molecule, the smaller the pKa. The more basic a molecule, the higher the pKa

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34
Q

Nucleophile

A

Like to form new bonds to electrophiles (donate e-, Lewis bases). Nucleophilicity increases as electronegativity, and leaving group quality, decreases. Ex/ Anions, pi bonds, *alcohols&amines (require a neutral or basic solvent)

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35
Q

Polar solvents

A

Dissolve nucleophiles and allow for reactants to mix together. They assist in the movement of e-

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36
Q

Nonpolar solvents

A

Do not allow for dissolution of nucleophiles. They are best used to halt enzymatic activity.

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37
Q

Polar protic solvent

A

Has the ability to hydrogen bond

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38
Q

Polar aprotic solvent

A

Can not hydrogen bond

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39
Q

Electrophiles

A

Have a positive charge or (+) polarized atom that accepts an e- pair when forming bonds with a nucleophile. Electrophile strength is determined by a molecules ability to accept and e- pair. Ex/ carbonyls, carbocation

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40
Q

Electrophillic addition

A

when a nucleophile attacks an electrophile that is a double or triple bond

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41
Q

Electrophilic aromatic substitution

A

process where an electrophile attacks an aromatic ring forming a carbocation. That carbocation is electrophilic and can undergo substitution with a base

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42
Q

Heterolytic reactions

A

opposite of coordinate covalent bond formation where a bond is broken and both e- are given to 1 of the products

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43
Q

SN1 reaction

A

Unimolecular substitution. The 1st step generates the carbocation and a leaving group (rate limiting)
Carbocation stability: tertiary > secondary > primary

44
Q

SN2 reaction

A

Bimolecular substitution. The only step in the rxn occurs when the nucleophile attacks the compound and the leaving group leaves at the same time
It is called a concerted reaction because it only has 1 step (rate limiting)

45
Q

Chemoselectivity

A

The preferential reaction of one functional group compared to others in a molecule. This is the most reactive region in a molecule. Ex/ a reducing reagent will react with a carboxylic acid over a alcohol in the same molecule

46
Q

Steric protection

A

used as a tool in the synthesis of desired molecules by preventing the formation of alternative products

47
Q

Electron withdrawing groups

A

Increase acidity

48
Q

Electron donating groups

A

Decrease acidity. Ex/ -CH3, -OCH3, -OH, -NH2

49
Q

Mesylate

A

Used to make alcohols good leaving groups because it is relatively inert and does not contain an acidic proton. Contains the functional group -SO₃CH₃

50
Q

Tosylate

A

Used to make alcohols good leaving groups because it is relatively inert and does not contain an acidic proton. It contains the group - SO₃C₆H₄CH₃

51
Q

Acetal

A

Primary carbon with 2 -OR groups and a H atom. Formed when 2 equivalents of an alcohol attacks an aldehyde

52
Q

Ketal

A

Secondary carbon with 2 -OR groups. Formed when 2 equivalents of an alcohol attacks a ketone

53
Q

Quinone

A

produced when a phenol is treated with an oxidizing agent

54
Q

Hydroxyquinone

A

same structure as quinones except they have 1 or more hydroxy groups attached

55
Q

Ubiquinone

A

Biologically active quinone associated with complexes I, II, III of the ETC. It is lipid soluble due to the long alkyl chain

56
Q

Acetylation

A

Reaction that occurs when an acetyl group (RC=O) is attached to a group

57
Q

Imine

A

Formed when ammonia attacks a carbonyl and water is lost. It has a N that is doubled bonded to a C

58
Q

Tautomers

A

2 isomers that differ in the placement of a proton and double bond

59
Q

α-racemization

A

if an aldehyde or ketone has a chiral α-carbon, it will become a racemic mixture during tautomerization

60
Q

Enamine

A

tautomer of imine

61
Q

Aldol condensation

A

where an aldehyde or ketone acts as a electrophile (keto form) and then a nucleophile (enolate form) to form a C-C bond

62
Q

Retro-aldol reaction

A

This is a reverse of the condensation reaction where 1 molecule is broken into 2 by breaking the bonds between the α and β carbons of the carbonyl (a C-C bond)

63
Q

Gringard reaction

A

This is an organometallic chemicalreactionin which alkyl, vinyl, or aryl-magnesium halides (Grignard reagent) add to a carbonyl group in an aldehyde or ketone

64
Q

Methanoic acid common name

A

Formic acid

65
Q

Ethanoic acid common name

A

Acetic acid

66
Q

Dimer

A

pairs of molecules connected by H bonds

67
Q

Lactams

A

amides that are cyclic

68
Q

Lactones

A

cyclic esters

69
Q

Decarboxylation

A

intermolecular reaction that occurs with β-keto acids and β-dicarboxylic acids. It results in the loss of a carboxyl group in a carboxylic acid as CO₂

70
Q

Saponification

A

Long chain carboxylic acids are reacted with NaOH (or LiOH) to form salts (R-COO-Na+) capable of solvating nonpolar organic cmpds. The longer the chain in the salt, the better the emulsifying agent (soap)

71
Q

Fisher esterification

A

under acidic conditions, carboxylic acids and alcohols condense into esters

72
Q

Reactivity of carboxylic acid derivitives

A

Acid anhydrides > carboxylic acids > esters > amides

73
Q

Transesterification

A

when an alcohol acts as a nucleophile, attacks an ester, and displaces the esterifying group (becomes a alcohol)

74
Q

Hydrolysis

A

cleavage of a bond with the addition of water

75
Q

Strecker synthesis

A

A mechanism that uses aldehydes to form amino acids in the lab. The identity of the aldehyde determines the identity of the amino acid

76
Q

Gabriel synthesis

A

Process of using alkyl halides to produce primary amines. Primary amines can be used to make amino acids

77
Q

Spectroscopy

A

measures the energy differences between states of a molecular system by determining the frequencies of EMR absorbed

78
Q

IR spectroscopy

A

measures molecular vibrations which are seen as bending, stretching, or a combination of different types
Range: 40 - 4000 cm⁻¹ (2500 - 25,000 nm)

79
Q

Hydroxyl IR frequency

A

(broad peak) - 3300 for alcohols and 3000 for carboxylic acids

80
Q

Carbonyl IR frequency

A

(sharp peak) - 1700

81
Q

Amine IR frequency

A

(sharp peak) - 3300

82
Q

UV spectroscopy

A

measures the wavelength of absorbance when UV light is passed through a dissolved substance. It is most useful for studying compounds with double bonds or heteroatoms with lone pairs that create conjugated systems

83
Q

Conjugated molecules

A

those with unhybridized p orbitals

84
Q

Extraction

A

the transfer of a dissolved compound from a starting solvent into a solvent where the product is soluble

85
Q

Immiscible

A

layers that do not mix

86
Q

Aqueous phase

A

contains polar solutes

87
Q

Organic phase

A

contains nonpolar solutes

88
Q

Sequestration

A

This is the removal of ions from solution by another type of molecule or ion through complex formation

89
Q

Distillation

A

separates liquids based on differences in boiling points by evaporation and condensation

90
Q

Simple distillation

A

The max BP is 150℃ and there needs to be a 25℃ difference between the 2 liquids

91
Q

Vacuum distillation

A

used when we want to distill a liquid with a BP over 150℃

92
Q

Superheating

A

occurs when the liquid is heated past its BP without vaporization

93
Q

Fractional distillation

A

used when we want to separate 2 liquids with similar BP (less than 25℃ apart)

94
Q

Chromatography

A

Physical and chemical properties are used to separate and identify compounds in a mixture based on affinity to the stationary phase. Most chromatography techniques use a polar stationary phase and a nonpolar mobile phase.
Lower the affinity —> faster the elution
Higher the affinity —> slower the elution

95
Q

Stationary phase

A

The solid medium or absorbant

96
Q

Thin layer chromatography

A

Uses a silica gel (polar, hydrophilic) or alumina adherent for the stationary phase to separate non-volatile mixtures based on polarity. Polar stationary phase, nonpolar mobile phase

97
Q

Retention factor

A

distance spot moved / distance solvent front moved

98
Q

Column chromatography

A

Similar to TLC except that it uses a column filled with an absorbent (like silica). It allows for greater absorption

99
Q

Ion exchange chromatography

A

column chromatography that uses beads in the column coated with charged substances that attack or bind compounds with the opposite charge

100
Q

Size exclusion chromatography

A

Uses beads in the column that contain tiny pores of varying sizes. Large compounds can not fit so they move around them and travel faster. Small compounds are slowed down and retained longer

101
Q

Affinity chromatography

A

uses a compound in the column that has a high affinity for the target compound

102
Q

Gas chromatography (GC)

A

The eluent is a gas. The absorbent is a crushed metal or polymer in a column. Molecules with the lowest MW and weakest intermolecular bonds will migrate fastest and be the first peak on a GC trace

103
Q

Stereospecific

A

A reaction preferentially yields a specific conformation of product over the other. Ex/ Sn2 rxn

104
Q

Resolving agents

A

A chiral molecule. Can be used to separate racemic mixtures by introducing a new chiral center to each

105
Q

Normal phase high performance liquid chromatography (HPLC)

A

Polar stationary phase, nonpolar mobile phase. Molecules with similar polarity to the stationary phase have longer retention times

106
Q

Reverse phase HPLC

A

Nonpolar stationary phase, polar mobile phase. The only type of chromatography that reverses the affinity for each phase

MCAT (7 decks)

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