Organic Chemistry For Iitjee

Front 1

Erythro

Back 1

a

xCy

xCy

b

Front 2

Threo

Back 2

a

xCy

yCx

b

Front 3

D configuration

Back 3

| COOH

HCOH or HCNH2

CH2OH |

Front 4

L configuration

Back 4

| COOH

HOCH or NH2CH

CH2OH |

Front 5

Methyl halide with highest dipole moment

Back 5

CH3Cl

Front 6

Grove's process

Back 6

ROH + HCl/ZnCl2 ----> RCl

Front 7

Lucas Test

Back 7

Alcohol is converted to chloride with HCl/ZnCl2 (Lucas reagent); white turbidity occurs. 3° react within a minute; 2° under 5 minutes; 1° do not react.

Front 8

Finkelstein reaction

Back 8

Iodination of alkyl halide (with NaI in acetone, with heat).

Front 9

Swart's reaction

Back 9

Fluorination of alkyl halide (with AsF3, SbF3, AgF, Hg2F2, CoF3)

Front 10

Birnbaum Simonini reaction

Back 10

RCOOAg + I2 ----> RCOOR +AgI

Front 11

Sandmeyer's reaction

Back 11

Diazonium salt (ArN2Cl) with CuCl2 / CuBr2 / KI / HBF4 gives ArX.

Front 12

Insecticide (C6H6Cl6) [name]

Back 12

Gammexane / Lindane / gamma-isomer (aaaeee)

Front 13

True/false:

1. Alkyl halides are more inflammable than alkanes.

2. RX (pure) is colorless, even on exposure to light.

3. Due to high electronegativity of halogens, alkyl halides can form hydrogen bonds, and hence, are soluble in water, but insoluble in organic solvents.

4. Bond stability order: CF > CCl > CBr > CI.

5. Alkalis cannot hydrolyse isocyanides.

6. Aliphatic alcohols react with HCl, even in the absence of ZnCl2, in Lucas test.

7. Wurtz reaction is not given by both 2° and 3° alkyl halides.

8. Thiols are more acidic than alcohols.

9. Due to stronger -I effect at ortho than para of nitro group, o-nitrophenol is more acidic than p-nitrophenol.

Back 13

1. False

2. False (RBr and RI develop color.)

3. False

4. True

5. True

6. False (only 3° can react in the absence of ZnCl2.)

7. False (only 3° halides do not give Wurtz reaction.)

8. True

9. False (H-bonding of ortho isomer decreases acidity.)

Front 14

Dow's Process (with regards to Organic Chemistry)

Back 14

Chlorobenzene to phenol at high temperature and pressure.

Front 15

Gattermann-Koch aldehyde synthesis

Back 15

Benzene + CO + HCl + AlCl3 ----> Benzaldehyde (under high pressure)

This is different from Gattermann aldehyde synthesis.

Front 16

Gattermann aldehyde synthesis

Back 16

Benzene + HCN + HCl + AlCl3 ----> (hydrolysis) ----> Benzaldehyde

Front 17

Von Richter Reaction

Back 17

Halonitrobenzene --(KCN / 150° C)--> Halocyanobenzene (entry of -CN ortho to -NO2 and expulsion of -NO2).

Front 18

Freon

Back 18

Chlorofluro compounds of methane and ethane

Front 19

Alcoholic Proof

Back 19

Twice the percentage by volume of alcohol, in an ethanol-water mixture.

Front 20

True/False:

False:

1. Di-Sulphonation followed by nitration of phenol gives better yield of picric acid than nitration alone.

2. Phenol turns pink on exposure to air and light, due to hydration.

3. On exposure to air and light for a long time, ethers react with nitrogen to form explosives.

4. In fries rearrangement of phenolic esters, o- form dominate at low temperature, and p- form at high temperature, due to -I effect of -OH group.

5. 3° RX should not be used for Williamson ether synthesis.

Back 20

1. True (In the latter, Phenol is oxidized to benzoquinone.)

2. False (Due to oxidation to quinone and resultant formation of phenoquinone.)

3. False (Peroxides, that decompose violently, are formed.)

4. False

5. True

Front 21

Dakin Reaction

Back 21

o/p-C6H4-CHO-(OH/NH2) ---(1. H2O2/NaOH ; 2. H3O+)---> (Replace -CHO with -OH)

Front 22

Ebs Persulphate oxidation

Back 22

Phenol with alkaline K2S2O8, followed by hydrolysis gives Quinol.

Front 23

Riemer-Tiemann Reaction

Back 23

Phenol + CHCl3 + aq. NaOH ----> o/p-hydroxybenzaldehyde

Front 24

Kolbe's reaction or Kolbe-Schmitt reaction

Back 24

Sodium phenoxide + CO2 --(400K / 6 atm)--> Salicylic acid

Sodium phenoxide + CO2 --(430 K / 6atm)--> p-hydroxy benzoic acid

Front 25

Vilsmeier reaction

Back 25

Phenol with dimethyl formamide and POCl3 gives o-hydroxybenzaldehyde.

Front 26

Ledderer Mannasse reaction

Back 26

Phenol with formaldehyde (with acid/base) gives hydroxy benzyl alcohol.

Front 27

Pinacol - Pinacolone rearrangement

Back 27

Vicinal diols in the presence of an acid undergo this reaction, forming ketones, via dehydration, followed by rearrangement.

Front 28

Williamson Synthesis

Back 28

RX + R'ONa ----> ROR'

(X is a halide, but can also be RSO3- or ArSO3-)

Front 29

Claisen Rearrangement reaction

Back 29

Aryl/Alkyl allyl ethers undergo a rearrangement when heated in an inert solvent; the alkyl group migrates, preferably to ortho, or para position.

This differs from Claisen Condensation and Claisen-Schmidt reaction.

Front 30

Fries Rearrangement reaction

Back 30

Phenolic esters with AlCl3 rearrange to form o- or p- acyl phenols.

Front 31

Jones reagent

Back 31

Chromic acid in acetone (with optionally, water)

Oxidises 1° and 2°alcohols to aldehyde (acid, if aqueous) and ketones without affecting double or triple bonds. Should not be used in the presence of acid sensitive groups.

Front 32

Collin's reagent or Collin-Ratcliff reagent

Back 32

CrO3 in pyridine and dichloro methane.

A mild oxidizing agent for alcohols containing acid sensitive groups.

Front 33

Oxidation with NaOCl

Back 33

Oxidises sec-alcohols without affecting primary.

Front 34

Kucherov reaction

Back 34

Hydration of alkyne by acid (H2SO4) and Hg2+ to alkenol - ketone / aldehyde.

Front 35

Nef reaction

Back 35

Conversion of nitro alkanes to carbonyls.

Front 36

Stephen's reaction

Back 36

Hydrolysis of cyanide to aldehyde, with SnCl2/HCl.

Front 37

Hell Volhard Zelinskey reaction

Back 37

Reaction of carboxylic acid with Cl2/Br2 in the presence of red phosphorus to yield alpha- (mainly)Cl /(but only)Br -acid.

Front 38

What happens when...

1. Alpha-hydroxy acids are heated?

2. Beta-hydroxy acids are heated?

3. Alpha-hydroxy acids are heated with dil. H2SO4?

4. Beta-hydroxy acids are heated with dil. H2SO4?

Back 38

1. Cyclic diesters are formed.

2. Alpha-beta unsaturated acid is formed.

3. Aldehyde/ketone and formic acid is formed.

4. Alpha-beta unsaturated acid is formed.

Front 39

Difference between benzyl, benzo, benzal?

Back 39

Benzo : PhC

Benzal : PhCH

Benzyl: PhCH2

Front 40

Claisen Condensation

Back 40

Two molecules of an ester, or an ester and a carbonyl compound, condense in the presence of a base (NaOEt) to give beta-keto-ester. This differs from Claisen Rearrangement and Claisen-Schmidt reaction.

Front 41

Schmidt Rearrangement Reaction

Back 41

Carboxylic acid with hydrazoic acid (with H2SO4) gives acid azide, which on heating gives alkyl isocyanate. This yields 1° amine on hydrolysis.

Front 42

Claisen-Schmidt Reaction

Back 42

Carbonyl compounds lacking alpha-H undergo aldol condensation with aldehydes/ketones containing alpha-H.

This differs from Claisen Rearrangement reaction and Claisen Condensation.

Front 43

Hofmann Bromamide Rearrangement (Degradation Reaction)

Back 43

Acid amides with Br2/Cl2 and alkali give primary amine, containing 1 C atom less than the parent.

Front 44

Dieckmann Condensation

Back 44

Diester containing alpha-H undergoes intramolecular Claisen condensation in the presence of a base (NaH/EtOH) to form a ring (generally 5, 6 or 7 membered).

Front 45

Lossen Rearrangement Reaction

Back 45

The Lossen rearrangement is the conversion of a hydroxamic acid to an isocyanate, via the formation of an O-acyl, sulfonyl, or phosphoryl intermediate hydroxamic acid O-derivative and then conversion to its conjugate base.

Front 46

Fenton's reagent

Back 46

A mixture of FeSO4 or acetate and H2O2 is Fenton's reagent, an oxidising reagent. (This involves the formation of OH radical.)

Front 47

Curtius Rearrangement reaction

Back 47

Acid azide, on heating in non polar solvent, rearranges to give alkyl isocyanate.

Front 48

Wolff Rearrangement

Back 48

Diazoketone, on treatment with Ag2O, rearranges to ketene, eliminating N2.

Front 49

Victor Meyer's Test

Back 49

Test for distinguishing alcohols:

Alcohol --> Iodide --> Nitrate --> Nitrolic acid, Pseudo nitrole, nil --(NaOH)--> (red, with 1°alcohol), (blue, with 2°alcohol), (colorless, with 3°alcohol) respectively

Front 50

Dunstan's test (for Glycerol)

Back 50

Phenolphthalein drops in borax solution give pink colour. Addition of glycerol to this solution discharges pink colour in cold, which however reappears on heating and again disappears on cooling. This in Dunstan's test for glycerine.

Front 51

Bouveault-Blanc Reduction

Back 51

Aldehyde, ketones and esters can be reduced to alcohols, in the presence of excess Na and ethanol.

Front 52

Product of reaction of alkyl borate (R3B) with:

1. H2O2 / OH-

2. CH3COOH

3. AgNO3

4. X2 (halogen, mainly Br2)

Back 52

1. Alcohol (Anti-Markovnikov)

2. Alkane

3. R-R

4. RX