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MCAT 1000 Kaplan > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

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MCAT flashcards
1
Q

Isomers that can convert by changing the location of a proton.

A

Tautomers

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2
Q

A type of diastereomers with different arrangements of substituents about an immovable bond.

A

Cis-Trans Isomers

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3
Q

A species that tends to donate electrons to another atom. With the same attacking atom (OH^‐, CH3O^‐) in aprotic solvents, nucleophile strength correlates to basicity. In protic solvents and in situations where the attacking atom is different (OH^‐, SH^‐), nucleophile strength correlates to smaller size.

A

Nucleophile

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4
Q

Stereoisomers that are not mirror images of each other. Diastereomers differ in their configurations at at least one chiral center and share the same configuration at at least one chiral center. They have similar chemical properties but different physical properties.

A

Diastereomers

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5
Q

Describes groups on a cyclic molecule that are perpendicular to the plane of the molecule, pointing straight up or down.

A

Axial

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6
Q

Increased energy that results when molecules assume eclipsed or gauche staggered conformations.

A

Torsional Strain

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7
Q

A functional group containing a nitrile (−C≡N) and a hydroxyl group.

A

Cyanohydrin

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8
Q

A method of synthesizing amino acids that uses potassium phthalimide and diethyl bromomalonate followed by an alkyl halide; two substitution reactions are followed by hydrolysis and decarboxylation.

A

Gabriel (Malonic-Ester) Synthesis

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9
Q

Describes two solvents that will not mix with or dissolve each other.

A

Immiscible

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10
Q

Describes groups that pull electron density away from another atom; stabilizes negative charges and destabilizes positive charges while increasing acidity.

A

Electron-Withdrawing

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11
Q

The phenomenon of atoms pushing electron density towards surrounding atoms; in NMR spectroscopy, pulls the group further upfield on the spectrum. Deshielding is the opposite - the pulling of electron density by surrounding atoms; in NMR, pulls a group further downfield on the spectrum.

A

Shielding

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12
Q

Molecules that have the same molecular formula but different connectivity; also called constitutional isomers.

A

Structural Isomers

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13
Q

A compound that has a carbonyl group bonded to nitrogen. Amides are named by dropping the -oic acid in the corresponding carboxylic acid and adding -amide. Substituents attached to nitrogen are listed as prefixes and are preceded by N-.

A

Amide

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14
Q

A molecule that either does not contain a chiral center or contains chiral centers and a plane of symmetry; as such, it has a superimposable mirror image.

A

Achiral

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15
Q

Characteristics of compounds that do not change chemical composition, such as melting point, boiling point, solubility, odor, color, and density.

A

Physical Properties

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16
Q

A type of bond that links the sugar moieties of adjacent nucleotides in DNA.

A

Phosphodiester Bond

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17
Q

A stereoisomer with an internal plane of symmetry. Meso compounds are optically inactive.

A

Meso Compound

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18
Q

Compounds consisting of only carbons and hydrogens bonded with σ bonds. As chain length increases, boiling point, melting point, and density increase. However, chain branching decreases both boiling point and density.

A

Alkanes

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19
Q

Molecules that have the same molecular formula but different connectivity; also called structural isomers.

A

Constitutional Isomers

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20
Q

Nonsuperimposeable stereoisomers that are mirror images of each other. Enantiomers differ in configuration at every chiral center but share the same chemical properties in a nonstereospecific environment. Their optical activities are exactly opposites of each other.

A

Enantiomers

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21
Q

A method used to separate a component in a mixture by exploiting its solubility properties. Two solvents are usually used (one aqueous and one organic), and the component of interest will be soluble in one phase, while the impurities will be soluble in the other.

A

Extraction

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22
Q

A type of chromatography that uses silica gel or alumina on a card as the medium for the stationary phase.

A

Thin-Layer Chromatography (TLC)

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23
Q

A functional group containing two carbonyls separated by an oxygen atom (RCOOCOR); often the condensation dimer of a carboxylic acid.

A

Anhydride

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24
Q

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

A

Newman Projection

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25
Q

Describes groups that push additional electron density toward another atom; stabilizes positive charges and destabilizes negative charges while decreasing acidity.

A

Electron-Donating

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26
Q

Describes the orbital in which an electron is found; possible values range from -l to +l.

A

Magnetic Quantum Number (m{l})

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27
Q

The complete loss of a carboxyl group as carbon dioxide.

A

Decarboxylation

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28
Q

Configurational isomers that have different spatial arrangements of substituents, which affects the rotation of plane-polarized light.

A

Optical Isomers

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29
Q

An -OH group; seen in alcohols, hemiacetals and hemiketals, carboxylic acids, water, and other compounds.

A

Hydroxyl Group

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30
Q

A technique that measures the alignment of magnetic moments from certain molecular nuclei with an external magnetic field; can be used to determine the connectivity and functional groups in a molecule.

A

Nuclear Magnetic Resonance (NMR) Spectroscopy

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31
Q

A double bond between a carbon and an oxygen.

A

Carbonyl

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32
Q

A functional group that contains a carbon atom bonded to two -OR groups, an alkyl chain, and a hydrogen atom.

A

Acetal

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33
Q

A standardized measure of a compound’s ability to rotate plane-polarized light.

A

Specific Rotation ([α])

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34
Q

A separation technique that uses the retention time of a compound in the mobile phase as it travels through the stationary phase two separate compounds with different chemical properties.

A

Chromatography

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35
Q

A compound that has a nonterminal carbonyl group. Ketones are named by replacing the -e in the corresponding alkane with -one.

A

Ketone

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36
Q

A compound that has a carbonyl as a terminal group. Aldehydes are named by replacing the -e in the corresponding alkane with -al. Formaldehyde, acetaldehyde, and propionaldehyde are common names used for the simplest aldehydes.

A

Aldehyde

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37
Q

A compound that has a -COOH terminal group. Carboxylic acids are named by replacing the -e in the corresponding alkane with -oic acid. Formic acid and acetic acid are common names for the simplest carboxylic acids: methanoic acid and ethanoic acid, respectively.

A

Carboxylic Acid

38
Q

A technique that measures molecular vibrations at different frequencies, from which specific bonds can be determined; functional groups can be inferred based on this information.

A

Infrared (IR) Spectroscopy

39
Q

Describes groups on a cyclic molecule that are in the plane of the molecule.

A

Equatorial

40
Q

Isomers that can only interconvert by breaking bonds; include enantiomers, diastereomers, and cis-trans isomers.

A

Configurational Isomers

41
Q

A cyclic ester; named according to the number of carbon atoms other than the carbonyl carbon and for the straight-chain form of the compound.

A

Lactone

42
Q

A compound that has a -COOR group. Esters are named as alkyl or aryl alkanoates.

A

Ester

43
Q

Derived from phosphoric acid, the molecule that forms high-energy bonds for energy storage in nucleotide triphosphates like ATP; also used for enzyme regulation.

A

Inorganic Phosphate (P{i})

44
Q

The resonance form of a carbonyl that has a carbon-carbon double bond (ene) and an alcohol (-ol).

A

Enol

45
Q

The exact spatial arrangement of atoms or groups in a chiral molecule around a single chiral atom, designated by (R) or (S).

A

Absolute Conformation

46
Q

Compounds with the same molecular formula and connectivity but different arrangements in space. Stereoisomers include cis-trans isomers, diastereomers, enantiomers, conformational isomers, and meso compounds.

A

Stereoisomers

47
Q

Stereoisomers that differ by rotation about one or more single bonds, usually represented using Newman projections.

A

Conformational Isomers

48
Q

An arbitrary variable used to plot NMR spectra; measured in parts per million (ppm).

A

Chemical Shift (δ)

49
Q

“Electron-loving” atoms with a positive charge or positive polarization; can accept an electron pair when forming new bonds with a nucleophile.

A

Electrophiles

50
Q

The bonding molecular orbital formed by head-to-head or tail-to-tail overlap of atomic orbitals; all single bonds are σ bonds.

A

Sigma (σ) Bond

51
Q

A technique that measures absorbance of ultraviolet light of various wavelengths passing through a sample.

A

Ultraviolet (UV) Spectroscopy

52
Q

An analog of frequency used for infrared spectra instead of wavelength.

A

Wavenumber

53
Q

The process that transforms one ester to another when an alcohol acts as a nucleophile and displaces the alkoxy group on an ester.

A

Transesterification

54
Q

Describes the shell in which an electron is found; values range from 1 to∞.

A

Principal Quantum Number (n)

55
Q

The pull of electron density across σ bonds.

A

Induction

56
Q

A liquid (or a gas in gas chromatography) that is run through the stationary phase in chromatography.

A

Mobile Phase

57
Q

A type of chromatography used to separate vaporizable compounds; the stationary phase is a crushed metal or polymer and the mobile phase is a nonreactive gas.

A

Gas Chromatography (GC)

58
Q

A functional group that contains a carbon atom bonded to one -OR group, one -OH group, and two alkyl chains.

A

Hemiketal

59
Q

In an IR spectrum, the region of 1400 to 400 cm^‐1 where more complex vibration patterns, caused by the motion of the molecule as a whole, can be seen; it is characteristic of each individual molecule.

A

Fingerprint Region

60
Q

The prevention of a reaction at a particular location in a molecule by substituent groups around the reactive site.

A

Steric Hindrance

61
Q

A functional group that contains a carbon atom bonded to one -OR group, one -OH group, an alkyl chain, and a hydrogen atom.

A

Hemiacetal

62
Q

A mixture that contains equal amounts of (+) and (-) enantiomers. Racemic mixtures are not optically active.

A

Racemic Mixture

63
Q

The carbon adjacent to a carbonyl; in amino acids, the chiral stereocenter in all amino acids except glycine.

A

α-Carbon

64
Q

A double bond between a carbon and a nitrogen.

A

Imine

65
Q

A form of chromatography in which a small sample is put into a column that can be manipulated with sophisticated solvent gradients to allow very refined separation and characterization; formerly called high-pressure liquid chromatography.

A

High-Performance Liquid Chromatography (HPLC)

66
Q

The lowest-energy molecular orbital that does not contain electrons; in UV spectroscopy, electrons are excited from the HOMO to the LUMO.

A

Lowest Unoccupied Molecular Orbital (LUMO)

67
Q

Describes the intrinsic spin of the two electrons in an orbital by arbitrarily assigning one of the electrons a spin of +1/2 and the other a spin of -1/2.

A

Spin Quantum Number (M{s})

68
Q

A ratio used in thin-layer chromatography to identify a compound; calculated as how far the compound traveled relative to how far the solvent front traveled.

A

Retardation Factor (R{f})

69
Q

The bonding molecular orbital formed when two parallel p-orbitals share electrons; exists as electron clouds above and below the σ bond between the two nuclei.

A

Pi (π) Bond

70
Q

The highest-energy molecular orbital containing electrons; in UV spectroscopy, electrons are excited from the HOMO to the LUMO.

A

Highest Occupied Molecular Orbital (HOMO)

71
Q

A reaction in which an aldehyde or ketone acts as both the electrophile and nucleophile, resulting in the formation of a carbon-carbon bond in a new molecule called an aldol.

A

Aldol Condensation

72
Q

An indication of the hypothetical charge that an atom would have if all of its bonds were completely ionic.

A

Oxidation State

73
Q

Increased energy that results when nonadjacent atoms or groups compete for the same space; also called steric strain.

A

Nonbonded Strain

74
Q

A molecule or carbon atom bonded to four different groups and without a plane of symmetry; thus, it is not superimposable upon its mirror image and has an enantiomer.

A

Chiral

75
Q

A compound that can be created from a carboxylic acid by nucleophilic acyl substitution; includes anhydrides, esters, and amides.

A

Carboxylic Acid Derivative

76
Q

The prevention of the formation of alternative products using a protecting group such as a mesylate or tosylate.

A

Steric Protection

77
Q

The phase over which the mobile phase runs during chromatography; usually a solid material. Also called the absorbent.

A

Stationary Phase

78
Q

In NMR spectroscopy, a phenomenon that occurs when there are protons in such close proximity to each other that their magnetic moments affect each other’s appearance in the NMR spectrum by subdividing their peaks into subpeaks; also called splitting.

A

Coupling

79
Q

Describes the subshell in which an electron is found; possible values range from 0 to n - 1, with l = 0 representing the s subshell, l = 1 representing p, l = 2 representing d, and l = 3 representing f.

A

Azimuthal Quantum Number (l)

80
Q

A separation technique used to separate liquids with different boiling points. The mixture is heated slowly, and as the liquid with the lower boiling point changes to its gaseous form, it passes through a condenser, where it cools back into its liquid form.

A

Distillation

81
Q

Atoms or groups that can dissociate from the parent chain to form a stable species after accepting electron pairs. Weak bases tend to be good leaving groups.

A

Leaving Group

82
Q

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

A

Relative Configuration

83
Q

Laboratory technique that relies on measurement of the energy differences between the possible states of a molecular system by determining the frequencies of electromagnetic radiation (light) absorbed by the molecules or their response to a magnetic field.

A

Spectroscopy

84
Q

A method of synthesizing amino acids that uses condensation between an aldehyde and hydrogen cyanide, followed by hydrolysis.

A

Strecker Synthesis

85
Q

Characteristics of compounds that change chemical composition during a reaction; determines how a molecule will react with other molecules.

A

Chemical Properties

86
Q

Energy created in a cyclic molecule by angle strain, torsional strain, and nonbonded strain; determines whether a ring is stable enough to stay intact.

A

Ring Strain

87
Q

A cyclic amide; named according to the number of carbon atoms other than the carbonyl carbon.

A

Lactam

88
Q

A reaction that combines two molecules into one, with the loss of a small molecule.

A

Condensation Reaction

89
Q

Alternating single and multiple bonds that create a system of parallel unhybridized p-orbitals; thus, electrons can be shared between these orbitals, forming electron clouds above and below the plane of the molecule and stabilizing it.

A

Conjugation

90
Q

An alcohol with an aromatic ring; has slightly more acidic hydroxyl hydrogens than other alcohols.

A

Phenol

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