Organic Chemistry

Front 1

SN2

Back 1

Primary substrate (steric hindrance), no rearrangement, polar aprotic solvent ( no H bonding), complete stereo inversion, reaction rate = k [Nuc][Elect]

Front 2

SN1 substrate

Back 2

tertiary

Front 3

SN1 rearrangementss

Back 3

possible, from less stable to more stable

Front 4

SN1 solvent

Back 4

polar protic (H bonding) to stabilize carbocation

Front 5

Stereochemistry SN1

Back 5

racemic mixture

Front 6

SN1 rate law

Back 6

rate = k [electrophile]

Front 7

Dehydration of alcohols

Back 7

alcohol -> alkene, favored by strong H+ and high T, possible rearrangements

Front 8

Formation of haloalkanes

Back 8

alcohol + PBr3
alcohol + SOCl2

Front 9

E1 substrate

Back 9

tertiary

Front 10

E1 solvent

Back 10

protic, H bonding to stabilize carbocation

Front 11

E1 product

Back 11

major - more substituted alkene

Front 12

E1 rate law

Back 12

rate = k[haloalkane]

Front 13

E1 conditions

Back 13

high T, strong base

Front 14

E2 substrate

Back 14

tertiary

Front 15

E2 solvent

Back 15

polar aprotic, no H bonding

Front 16

E2 stereochemistry

Back 16

anti of proton and leaving group

Front 17

E2 rate law

Back 17

rate = k [base][haloalkane]

Front 18

HX additon to alkenes

Back 18

Markovnikov addition, racemic mixture, possible rearrangements

Front 19

HBr + peroxides addition

Back 19

no rearrangements , anti markovnikov, only for HBr

Front 20

Oxymercuration-Demercuration

Back 20

alkene - alcohol, Markovnikov addition, no rearrangement

Front 21

Hydroboration oxidation

Back 21

anti Markovnikov alcohol, BH3/H2O2, OH on less substituted carbon

Front 22

Hydrogenation of alkenes

Back 22

syn addition, only in the presence of catalyst

Front 23

Hydrogenation of alkynes with Lindlar catatlyst

Back 23

stops at alkene , syn addition

Front 24

Hydrogenation of alkynes with Na/NH3

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stops at alkene, trans addition

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Addition of X2 to alkenes

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intermediate halonium ion, positive charge on bridged halogen, anti addition, no rearrangements

Front 26

Epoxide formation

Back 26

alkene + peroxy acid = epoxide + carboxylic acid

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Epoxide hydrolysis results in

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trans diol

Front 28

In order to form cis diol need to react alkene with

Back 28

KMnO4 or OsO4

Front 29

Ozonolysis results in cleavage of double bond and formation of

Back 29

aldehydes and ketones

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Criteria for aromaticity

Back 30

1.cyclic system with unhybridized p orbitals
2.flat and planar
3.4n+2 e's

Front 31

Ortho para directors

Back 31

activating groups - NR2, OH, OR, amides, esters, R groups

Cl, Br, I deactivators but ortho para

Front 32

Meta directing

Back 32

e-n withdraawing groups
NR3, NO2, cyanide, ketones, carbox acids etc

Front 33

Acetal formation

Back 33

ketone + HCl/ROH - hemiacetal
hemiacetal + ROH (-H2O) - Acetal

Front 34

Extraction

Back 34

technique that allows separation of a substance from a mixture of substancesby adding a solvent that the compound of interest s highly soluble in

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Crystallization

Back 35

method of separation that relies on differential solubilities of two compounds in given solvent

Front 36

Thin layer chromatography

Back 36

compounds separated based on polarity

Front 37

Polar components move slower or faster?

Back 37

move slower since interact with polar stationary phase

Front 38

calculating R for TLC

Back 38

R = distance traveled/distance to solvent front

Front 39

Gas chromatography

Back 39

separation technique based on ifferent volatility

Front 40

Rates of movement in GC

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more volatile faster, less volatile slower

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Simple distillation

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when trace impurities need to be removed from relatively pure compound or in a mixture with significantly different boiling points

Front 42

Fractional distillation

Back 42

small difference in boiling points

Front 43

IR of alkenes

Back 43

double bond stretch at 1650 cm

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IR carbonyl

Back 44

1700

Front 45

IR alkynes

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2600

Front 46

IR nitriles

Back 46

2100

Front 47

IR OH

Back 47

36000

Front 48

CH stretch

Back 48

3000-3300

Front 49

What can be seen from NMR

Back 49

1.# of sets of peaks = # different H's
2. chemical shift - chemical environment
3.integration # - # of Hs in the set
4.splitting pattern - neighbours

Front 50

If protons near electronegative group - downfield or upfield?

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downfield and deshielded

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WHich amino acid is not chiral?

Back 51

glycine

Front 52

All animal amino acids have... configuration

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L, amino group on the left

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All carbohydrates have ... configuration

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D

Front 54

Amino acid is
a. basic
b. acidic
c. both

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c, amphoteric

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Hydrophobic amino acids

Back 55

either aliphatic or aromatic side chains

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Amino acid with aliphatic side chains

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glycine, alanine, valine, leucine, isoleucine

Front 57

Amino acids with aromatic side chains

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phenylalanine, tyrosine, tryptophan

Front 58

Hydrophilic amino acids

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acidic, basic and uncharged

Front 59

Acidic hydrophilic amino acids

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glutamic and aspartic amino acids

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Basic hydrophlic amino acids

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lysine, arginine and histidine

Front 61

Histidine - proton acceptor or donor?

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both, His goes both ways

Front 62

uncharged polar amino acids

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serie, threonine, asparagine, glutamine

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Sulfur containing amino acids

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methionine, cysteine

Front 64

Denaturation

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disruption of proteins shape w/out breaking peptide bonds

Front 65

Proteins can be denatured by

Back 65

urea, extremes of pH, extremes of temp, changes in salt concentration

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Primary structure

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amino acid sequence, determined by peptide bond

Front 67

Secondary structure

Back 67

hydrogen bonds between backbone groups

Front 68

Tertiary structure

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Hydrophobic/hydrophilic interactions

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Quaternary structure

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Various bonds between separate chains

Front 70

Formula of carbohydrate

Back 70

CnH2nOn

Front 71

What gives positive Benedicts test?

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aldehydes, ketones, hemiacetals

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What gives negative Benedicts test?

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acetals

Front 73

Soaps

Back 73

sodium salts of fatty acids
amphipathic, both hydrophilic and hydrophobic

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Fatty acids

Back 74

stored as fat, fat- triacylglycerol

Front 75

Triglyceride

Back 75

three fatty acids esterified to a glycerol

Front 76

Glycerol

Back 76

three hydroxyl groups can be esterified to fatty acids

Front 77

Saponification

Back 77

Triacylglycerol + NaOH ->>glycerol + 3 fatty acids