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MCAT Prep > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

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MCAT flashcards
1
Q

Isomers

A

same molecular formula but different structural arrangements

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2
Q

Structural Isomers

A

same molecular formula, different connectivity

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3
Q

Stereoisomers

A

Same molecular formula, same connectivity

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4
Q

Conformational Isomers

A

Type of stereoisomer, does not require bond breaking to interconvert (differs in rotation around single sigma bond)
-antistaggered, gauche, éclipsed, total eclipsed conformations

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5
Q

Configurational Isomers

A

Type of stereoisomer, does require bond breaking to interconvert
Form either diastereomers or enantiomers

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6
Q

Diastereomer

A

Type of configurational Isomer, superimposable mirror images
two chiral molecules, share same connectivity, NOT mirror images of each other

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7
Q

Enantiomer

A

type of configurational isomer, nonsuperimposable mirror images
Same connectivity, but opposite configurations at every chiral center
Same physical and chemical properties
DIFFERENT optical activity and reaction in chiral environments

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8
Q

Optical activity

A

rotation of plane polarized light around a chiral molecule

Direction can only be determined experimentally

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9
Q

Chirality

A

handedness, if the mirror image CANNOT be superimposed – meaning that the molecule DOES NOT have an internal plane of symmetry

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10
Q

Racemic mixture

A

when both + and - enantiomers are present in equal proportions

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11
Q

Cis-Trans Isomers

A

geometric isomers, type of diastereomer

substituents differ in position around an immovable bond

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12
Q

MESO compounds

A

internal mirror plane, Newman projections are the same

“chiral centers that HAS an internal plane of symmetry

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13
Q

E and Z configurations

A

describe absolute configuration around double bonds

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14
Q

R and S

A

describes chiral centers (stereo centers)
S: counter clockwise
R: Clockwise

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15
Q

sp3 hybridization

A

tetrahedral geometry
109.5 bond angle
carbons w/ all single bonds

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16
Q

sp2 hybridization

A

trigonal planar geometry
120 bond angle
carbons w/ one double bond

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17
Q

sp hybridization

A

linear geometry
180 bond angle
carbon w/ triple or 2 double bonds

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18
Q

acidic functional groups

A

alcohols
aldehydes
ketones
carboxylic acids

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19
Q

basic functional groups

A

amines

amides

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20
Q

SN1 Reaction

A

unimolecular nucleophilic substitution reaction
1. leaving group leaves forming carbocation, 2. Nu attacks planar carbocation = racemic mixture
-prefers highly sub carbons
-rate ONLY dependent on substrate
rate = k[substrate]

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21
Q

SN2 Reaction

A

bimolecular nucleophilic substitution reaction
1. Nu attacks @ same time leaving group leaves
Nu backside attack = inversion in stereochemistry
- rate dependent on substrate and Nu
rate = k[Nu][substrate]

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22
Q

phenols

A 
benzene rings w/ hydroxyl groups
ortho- adjacent carbons
meta- separated by one carbon
para- opposite sides of the ring
*are more acidic due to their delocalized charge of conjugate base
23
Q

oxidation of primary-OH by PCC

A

aldehyde

24
Q

oxidation of primary-OH by strong oxidizing agent

A

carboxylic acid

25
Q

oxidation of secondary-OH

A

ketone

26
Q

Tautomers

A

isomers, interconnected by moving a H and double bond ex: keto and enol forms

27
Q

physical properties of Carboxylic Acids

A

Polar, H bond very well
Increases boiling point
often dimers in solution
acidity is enhanced by resonance + e- that are donating

28
Q

COOH + Nu (ammonia or amine) =

A

amide forms

29
Q

COOH + Nu (alcohol) =

A

ester forms

30
Q

COOH + Nu (COOH) =

A

anhydride forms

31
Q

Saponification

A

long chain COOH (fatty acid) + strong base = salt (or soap)

32
Q

condensation reaction of COOH and OHs

A

ester

suffix -oate

33
Q

Nonpolar Nonaromatic Amino Acids (7)

A 
Alanine
Valine
Leucine
Isoleucine
Glycine
Proline
Methionine
34
Q

Aromatic Amino Acids (3)

A

tryptophan
Phenylalanine
Tyrosine

35
Q

Polar Amino Acids (5)

A 
Serine
Threonine
Asparagine
Glutamine
Cysteine
36
Q

Negatively Charged Amino Acids (2)

A

Aspartic Acid

Glutamic Acid

37
Q

Positively Charged Amino Acids (3)

A

(amines in their R groups)
Arginine
Lysine
Histidine

38
Q

Nonpolar nonromantic and aromatic amino acids both-

A

tend to be hydrophobic, reside in the interior

39
Q

Polar, negatively and positively charged amino acids both-

A

hydrophilic, reside on surface of proteins

40
Q

Strecker Synthesis

A

generates amino acids from an aldehyde

aldehyde + NH4Cl + KCN

41
Q

Gabriel Syntesis

A

generates amino acids from potassium phthalimide, diethyl bromomalonate, alkyl halide

42
Q

Infrared Spectroscopy

A

to appear, bond vibration changes bond dipole moment

43
Q

IR Spectroscopy: O-H peak

A

broad, around 3300 cm-1
(alcohols, water, COOH)
COOH may shift around 3000 cm-1

44
Q

IR Spectroscopy: N-H peak

A

sharp, around 3300 cm-1 (amines, imines, amides)

45
Q

IR Spectroscopy: C=O peak

A

sharp, around 1750 cm-1

aldehydes, ketones, COOH, amides, esters, anhydrides

46
Q

Nuclear Magnetic Resonance (NMR)

A
  • measures alignment of nuclear spin
  • determines connectivity of compound and functional groups
  • pulses push nuclei from lower energy (alpha) state to higher (beta) state
47
Q

Proton (H1) NMR

A

Integration: Area under the curve/peak is proportional to # of protons
Deshielding: protons occur when e- withdrawing groups pull e- away

48
Q

Proton (H1) NMR: aldehyde H

A

9-10 ppm

49
Q

Proton (H1) NMR: COOH Hs

A

10.5-12 ppm

50
Q

Proton (H1) NMR: aromatic Hs

A

6-8.5 ppm

51
Q

Chromatography: Stationary vs. Mobile Phase

A

Stationary: absorbent, usually a polar solid
Mobile: runs through the stationary phase, usually liquid or gas, elutes the sample through the stationary phase

52
Q

High affinity for the stationary phase =

A

smaller retardation factors

take longer to pass through

53
Q

low affinity for the stationary phase =

A

elute through more quickly

54
Q

Calculating Rf factor on thin layer chromatography

A

distance spot moved / distance solvent font moved

MCAT Prep (11 decks)

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