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Organic Chemistry Flashcards

(54 cards)

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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

Study These Flashcards
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

24
Q

oxidation of primary-OH by strong oxidizing agent

Study These Flashcards
A

carboxylic acid

25
oxidation of secondary-OH
ketone
26
Tautomers
isomers, interconnected by moving a H and double bond ex: keto and enol forms
27
physical properties of Carboxylic Acids
Polar, H bond very well Increases boiling point often dimers in solution acidity is enhanced by resonance + e- that are donating
28
COOH + Nu (ammonia or amine) =
amide forms
29
COOH + Nu (alcohol) =
ester forms
30
COOH + Nu (COOH) =
anhydride forms
31
Saponification
long chain COOH (fatty acid) + strong base = salt (or soap)
32
condensation reaction of COOH and OHs
ester | suffix -oate
33
Nonpolar Nonaromatic Amino Acids (7)
``` Alanine Valine Leucine Isoleucine Glycine Proline Methionine ```
34
Aromatic Amino Acids (3)
tryptophan Phenylalanine Tyrosine
35
Polar Amino Acids (5)
``` Serine Threonine Asparagine Glutamine Cysteine ```
36
Negatively Charged Amino Acids (2)
Aspartic Acid | Glutamic Acid
37
Positively Charged Amino Acids (3)
(amines in their R groups) Arginine Lysine Histidine
38
Nonpolar nonromantic and aromatic amino acids both-
tend to be hydrophobic, reside in the interior
39
Polar, negatively and positively charged amino acids both-
hydrophilic, reside on surface of proteins
40
Strecker Synthesis
generates amino acids from an aldehyde | aldehyde + NH4Cl + KCN
41
Gabriel Syntesis
generates amino acids from potassium phthalimide, diethyl bromomalonate, alkyl halide
42
Infrared Spectroscopy
to appear, bond vibration changes bond dipole moment
43
IR Spectroscopy: O-H peak
broad, around 3300 cm-1 (alcohols, water, COOH) COOH may shift around 3000 cm-1
44
IR Spectroscopy: N-H peak
sharp, around 3300 cm-1 (amines, imines, amides)
45
IR Spectroscopy: C=O peak
sharp, around 1750 cm-1 | aldehydes, ketones, COOH, amides, esters, anhydrides
46
Nuclear Magnetic Resonance (NMR)
- 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
Proton (H1) NMR
Integration: Area under the curve/peak is proportional to # of protons Deshielding: protons occur when e- withdrawing groups pull e- away
48
Proton (H1) NMR: aldehyde H
9-10 ppm
49
Proton (H1) NMR: COOH Hs
10.5-12 ppm
50
Proton (H1) NMR: aromatic Hs
6-8.5 ppm
51
Chromatography: Stationary vs. Mobile Phase
Stationary: absorbent, usually a polar solid Mobile: runs through the stationary phase, usually liquid or gas, elutes the sample through the stationary phase
52
High affinity for the stationary phase =
smaller retardation factors | take longer to pass through
53
low affinity for the stationary phase =
elute through more quickly
54
Calculating Rf factor on thin layer chromatography
distance spot moved / distance solvent font moved

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