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MCAT > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

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MCAT flashcards
1
Q

IUPAC Nomenclature for Alkanes

A

(1) Identify and name longest carbon chain (1C = Methane, 2C = ethane, 3C = propane, 4C = butane, 5C = pentane, etc.)
(2) Label carbons such that substituents have lowest possible #’s
(3) Identify all substituents (methyl, ethyl, etc.)
(4) Place substituents in alphabetical order

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2
Q

Priority of Substituents in IUPAC Nomenclature of Alkanes

A

Other functional groups have a suffix (when they are the highest-priority group): -COOH (-oic acid) is highest priority, followed by carboxylic acid derivatives, aldehydes/ketones (suffix: -al/-one, prefix: oxo-), alcohols (suffix: -ol, prefix: hydroxy), amines (suffix: -amine, prefix: amino-), thiols (suffix: thiol, prefix: mercapto-), and hydrocarbons

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3
Q

Resonance

A

When more than one equivalent Lewis structure can be drawn for a compound. Multiple structures indicate electron delocalization.

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4
Q

Aromatic Compounds

A

Conjugated cyclic molecules with planar structure + satisfy Huckle’s rule: having 4n + 2 pi electrons, where n is 0 or an integer

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5
Q

Cahn-Ingold-Prelog Rules for assigning priority to substituents

A

(1) Look at atoms directly connected to the stereocenter; heavier atoms have higher priority
(2) If two atoms are the same, move one atom further down the substituents and re-rank by substituents.
(3) Continue until a difference is encountered; multiple bonds are higher-priority than single bonds

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6
Q

E/Z System for double bonds

A

E if higher-priority substituents are on opposite sides of double bond, Z if higher-priority substituents are on the same side

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7
Q

R/S System for chiral system

A

Orient molecule such that lowest-priority substituent faces into the page and connect substituents from high to low priority; if doing so traces a clockwise pattern

Molecule is R; if counterclock-wise, S

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8
Q

Chirality

A

Non-superimposable mirror images (enantiomers)

C must have 4 different substituents. When there is more than one chiral center, enantiomers have opposite orientation at all chiral centers, while diasteromers only differ at some

For n chiral centers, there is a maximum of 2^n stereoisomers

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9
Q

Alcohol

A

RC - OH

-ol, hydroxy-

High melting/boiling point

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10
Q

Aldehyde

A

RC(O)H

-al, oxo-

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11
Q

Ketone

A

R(C=O)R’

-one, oxo-, keto-

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12
Q

Carboxylic Acids

A

-oic acid

R(C=O)OH

High melting/boiling point

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13
Q

Amide

A

R(C=O)NH2

-amide

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14
Q

Ester

A

R(C=O)OR’

-yl, -ate

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15
Q

Acid Anhydride

A

R(C=O)O(C=O)R’

-oic anhydride

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16
Q

Amine

A

R-NH2, R-NHR

-amine, amino-

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17
Q

Imine

A

R=NH, R=NR’

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18
Q

Enamine

A

RC=CNH, C=CNHR

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19
Q

Mild Oxidizing Agents

A

PCC

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20
Q

Strong Oxidizing Agent

A

NaCr2O7, K2Cr2O7, and CrO3

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21
Q

Mild Reducing Agent

A

NaBH4

22
Q

Strong Reducing Agent

A

LiAlH4

23
Q

Factors Affecting Acidity

A

Resonance

24
Q

Factors Affecting Reactivity

A

Electron-withdrawing groups, resonance, steric effect, strain

25
Q

Basic Idea for a Mechanism

A

An electrophile and a nucleophile form a bond

26
Q

Electrophile

A

An atom that ‘needs’ electrons (usually has positive or partial positive charge)

27
Q

Nucleophile

A

An atom that ‘needs’ to share its excess electrons (usually has negative or partial negative charge

28
Q

Sn1

A

Nucleophilic substitution with a first-order rate law (depends on substrate concentration only). Carbocation forms, then nucleophile attacks.

Favorable Factors: highly substituted carbons, polar protic solvent

29
Q

Sn2

A

Nucleophile substitution with a second-order rate law (depends on substrate and nucleophile concentration). Nucleophile performs ‘backside attack’ and kicks out leaving group, inverting the stereochemestry

Favorable Factors: Methyl/primary carbons, strong and non-bulky nucleophile, polar aprotic solvent

30
Q

Carboxylic Acid

A

C has a strong partial positive charge, is a good electrophile. Nucleophilic substitution is common, as in Fischer esterification and imine formation

Nucleophile Attacks carboxylic acid C, then leaving group is kicked off

31
Q

Nucleophilic Addition At Carbonyl C (C=O)

A

Hemiacetals (-R, -H, -OH, -OR’) formed from aldehydes, hemiketals (-R, -R’, -OH, -OR’’) from ketones. Reaction can repeat with excess alcohol to form acetals and ketals (another -OR group instead of -OH)

Nucleophile attacks carbonyl C without a leaving group

32
Q

Keto-Enol Tautomerism

A

Can be catalyzed by acid or base, a-hydrogen removal is critical in both (first step in base-catalyzed mechanism, second step in acid catalysis)

33
Q

Enolate Chemistry

A

Resonance-stabilized negative charge on a-carbon allows carbon to be a nucleophile

34
Q

Aldol Condensation

A

Nucleophilic a-carbon attacks electrophilic carbonyl C to form a new C-C bond

35
Q

Retro-Aldol

A

Reverse of the aldol condensation process

36
Q

Michael Addition

A

An Enolate attacks the B-carbon of an a,B-unsaturated aldehyde/ketone

37
Q

Robinson Annulation

A

Michael addition followed by aldol condensation

38
Q

Analytic Techniques

A

Identify features of a molecule or the molecule’s identity
- Often render the sample unusable in the future
- Examples: IR, NMR, UV-Vis, mass spec.

39
Q

Separation Techniques

A

Convert a mixture into multiple separate, pure samples (to the extent to which this is possible)
- Samples can then be analyzed or otherwise used later
- Examples: Distillation, extraction, chromatography, recrystallization, filtration

40
Q

Infrared (IR) Spectroscopy

A

Uses radiation with a frequency lower than that of visible light to vibrate bonds

C=O –> 1700 cm-1, sharp

O-H –> 3200-3600 cm-1, broad

41
Q

Nuclear Magnetic Resonance (NMR) Spectroscopy

A

Left side of spectrum = “downfield” = deshielded = close to e- withdrawing groups

Right side of spectrum = “upfield” = shielded = far from e- withdrawing groups

Area under peak corresponds to number of equivalent hydrogens

Splitting (singlet, doublet, … etc.) is determined by number of hydrogens on adjacent atom

42
Q

Ultraviolet-visible (UV-Vis) Spectroscopy

A

Useful to discern presence of conjugated/aromatic species

43
Q

Mass Spectroscopy

A

Helps determine molecular weight (m/z peak)

44
Q

Distillation

A

Separates liquids based on boiling point (BP)
- For BPs > 25° apart, use simple distillation
- For BPs < 25° apart, use fractional distillation
- For very high BPs, use vacuum distillation to lower atmospheric pressure (lower P = lower BPs)

45
Q

Extraction

A

Separates liquids based on solubility/acid-base properties
- Requires immiscible aqueous and organic layers in a seperatory funnel
- To send an acid into the aqueous layer, add base (deprotonate it)
- To send base into the aqueous layer, add acid (protonate it)

46
Q

Chromatography

A

Involves a mobile phase and a stationary phase with different properties

47
Q

TLC

A

Stationary phase is polar (usually silica) while mobile phase is a nonpolar solvent

Rf = (distance traveled by compound) / (distance traveled by solvent)

48
Q

Other forms of Chromatogrphy

A

Size-exclusion, cation-exchange, anion-exchange, and affinity chromatogrphy are all forms of column chromatography

49
Q

Gas Chromatography

A

Vaporizes sample and passes through a column, then measures retention time

50
Q

HPLC

A

Rapid method of column chromatography; polar stationary phase and nonpolar mobile phase for regular process; nonpolar stationary phase and polar mobile phase for reverse process (RP-HPLC)

51
Q

Other Separation Techniques

A

Recrystallization and Filtration

MCAT (6 decks)

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