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chem organic reactions Flashcards

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1
Q

free radical substitution rnc

A

limited X2, UV light

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2
Q

electrophilic addition rnc

A

br2 in CCl4

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3
Q

alkene to CH3-CH2(X)

A

Dry HX(g) / HX on CCl4

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4
Q

alkene to alcohol (CH3CH2OH)

A
  1. Conc H2SO4 followed by boiling/heating with water

2. Heat at high pressure with conc. H3PO4 as catalyst

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5
Q

alkene to alkane

A

(reduction)

  1. H2 gas in the presence of high T and P
  2. Pd catalyst at rtp
  3. Pt catalyst at rtp
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6
Q

alkene to diol

A

cold alkaline KMNO4 (oxidation)

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7
Q

alkene to ketone/carboxylic acid/ carbonic acid then to CO2/H20

A
  1. hot acidified KMNO4
  2. hot KMNO4, dilute H2SO4
  3. hot alkaline KMNO4
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8
Q

test for alkenes

A
  1. Add Br2 in CCl4, rtp in the dark
    (decolourisation of orange Br2 solution)
  2. Add cold alkaline KMNO4
    (formation of brown ppt of MnO2)
  3. Add hot acidified KMNO4
    (decolourisation of purple KMNO4 solution)
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9
Q

Alcohol to alkene

A

(elimination)

  1. Excess conc H2SO4, heat
  2. Al2O3 catalyst, heat
  3. Excess conc H3PO4, heat

(IMPORTANT!!)

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10
Q

halogenoalkane to alkene

A

(elimination)

NaOH in ethanol, heat

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11
Q

benzene to halogenoarene

A

X2 with anhydrous FeX3/AlX3/Fe

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12
Q

benzene to nitrobenzene

A

conc HNO3 and conc H2SO4, 55°C

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13
Q

benzene to alkylbenzene

A

CH3X with anhydrous FeX3/AlX3

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14
Q

alkylbenzene to 2 or 4 nitromethylbenzene

A

conc HNO3 and conc H2SO4, 30°C

(lower temperature is required as compared to benzene due to the presence of the methyl group, which activates the benzene ring, more susceptible to electrophilic substitution)

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14
Q

alkylbenzene to 2 or 4 nitromethylbenzene

A

conc HNO3 and conc H2SO4, 30°C

(lower temperature is required as compared to benzene due to the presence of the methyl group, which activates the benzene ring, more susceptible to electrophilic substitution)

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15
Q

methylbenzene to 2-chloromethylbenzene or 2-bromomethylbenzene

A

X2 with anhydrous FeX3/AlX3/Fe IN THE DARK

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16
Q

methylbenzene to CH2Cl(C6H5)

A

(FRS)

limited Cl2(g), UV light

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17
Q

methylbenzene to benzoic acid

A

KMNO4 in dilute H2SO4, heat (oxidation)

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18
Q

nucleophilic substitution (Sn2)

A

nucleophile (eg. OH-) with primary halogenoalkane

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19
Q

nucleophilic substitution (Sn1)

A

nucleophile (eg. OH-) with tertiary halogenoalkane

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20
Q

RX to ROH

A

NaOH (aq), heat

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21
Q

RX to ROR’

A

Na in excess alcohol (R’O- Na+), heat

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22
Q

RX to RCN

A

KCN in ethanol, heat under reflux

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23
Q

RCN to RCOOH

A

HCl(aq) / H2SO4(aq), heat under reflux

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24
Q

RCN to RCH2NH2

A
  1. LiAlH4 in dry ether
  2. H2 with Ni catalyst, heat
  3. H2 with Pd / Pt catalyst
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25
Q

RX to RNH2

A

Excess conc NH3 in ethanol, heat in sealed tube

IMPORTANT

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26
Q

halogenoalkane to alkene

A

KOH or NaOH in ethanol, heat

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27
Q

test for halogenoalkane

A

heat the compound with NaOH (aq), followed by the addition of dilute HNO3. Add AgNO3

if white ppt -> RCl present
if cream ppt -> RBr present
if yellow ppt -> RI present

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28
Q

relative ease of hydrolysis of halogenoalkanes

A

(slowest) RCl>RBr>RI (fastest)

due to breaking of C-X bond hence depends on C-X bond strength

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29
Q

reactivity difference between halogenarenes and halogenoalkanes

A

For halogenoarenes, C-X bond shorter and stronger than those in halogenoalkanes. Lone pair on X atom is delocalised into the pi electron cloud of the benzene ring, strengthening the C-X bond in the halogenoarenes due to presence of partial double bond character. In addition, the pi electron cloud of the benzene ring will repel the lone pair of electrons of the incoming nucleophile, rendering attack of the nucleophile difficult.

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29
Q

reactivity difference between halogenarenes and halogenoalkanes

A

For halogenoarenes, C-X bond shorter and stronger than those in halogenoalkanes. Lone pair on X atom is delocalised into the pi electron cloud of the benzene ring, strengthening the C-X bond in the halogenoarenes due to presence of partial double bond character. In addition, the pi electron cloud of the benzene ring will repel the lone pair of electrons of the incoming nucleophile, rendering attack of the nucleophile difficult.

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30
Q

halogenoalkenes do not undergo NS because ____________

A

the lone pair on the X atom is delocalised into the pi bond of the adjacent C C double bond, strengthening the C-X bond due to presence of partial double bond character, hence NS do not occur in normal condition.

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31
Q

relative ease of hydrolysis of acyl chloride compared to alkyl and aryl chlorides

A

fastest RCOCH3 > RCL > C6H5Cl (doesnt even occur)

for RCOCH3, the carbonyl atom is bonded to 2 electronegative atoms O and Cl, making carbonyl C atom highly electron deficient and very susceptible to NS.

for RCl, there is only one electronegative Cl bonded to the alkyl C atom. Hence the alkyl C atom is less electron deficient and less susceptible to NS.

for C6H5Cl, the lone pair of electrons on the Cl atom is delocalised into the benzene ring, strengthening the C-X bond due to presence of partial double bond character, hence NS does not occur.

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31
Q

relative ease of hydrolysis of acyl chloride compared to alkyl and aryl chlorides

A

fastest RCOCH3 > RCL > C6H5Cl (doesnt even occur)

for RCOCH3, the carbonyl atom is bonded to 2 electronegative atoms O and Cl, making carbonyl C atom highly electron deficient and very susceptible to NS.

for RCl, there is only one electronegative Cl bonded to the alkyl C atom. Hence the alkyl C atom is less electron deficient and less susceptible to NS.

for C6H5Cl, the lone pair of electrons on the Cl atom is delocalised into the benzene ring, strengthening the C-X bond due to presence of partial double bond character, hence NS does not occur.

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32
Q

solubility of alcohols in water decreases as no. of C atoms in the alcohol increases because ___________

A

the larger non polar R group makes the molecule more hydrophobic in nature. The extent of IDID between R groups of the molecule is more significant than the extent of hydrogen bonding between the alcohol molecules and the water molecules.

33
Q

alcohol to ester

A

COOH, conc H2SO4 catalyst, heat

34
Q

alcohol to ester pt 2

A

RCOCl (condensation)

35
Q

alcohol to aldehyde

A

K2Cr2O7 in dilute H2SO4, heat with immediate distillation

36
Q

alcohol to carboxylic acid

A
  1. K2CrO7 in dilute H2SO4, heat

2. KMNO4 in dilute H2SO4, heat

37
Q

aldehyde to carboxylic acid

A
  1. K2CrO7 in dilute H2SO4, heat

2. H2SO4 in dilute H2SO4, heat

38
Q

iodoform products for RCH(CH3)(OH) 4I2 and 6NaOH

A

RCOO-Na+ + CHI3 (yellow ppt) + 5NaI + 5H2O

39
Q

aldehyde to pri alcohol

A
  1. LiAlH4 in dry ether
  2. NaBH4 in ethanol
  3. H2 in Ni catalyst, high T and P
  4. H2 in Pt or Pd
40
Q

ketones to sec alcohol

A
  1. LiAlH4 in dry ether
  2. NaBH4 in ethanol
  3. H2 in Ni catalyst, high T and P
  4. H2 in Pt or Pd
41
Q

tests for alcohols

A
  1. add anhydrous PCl5 to compound
    (white fumes of HCl observed)
  2. heat the compound with KMNO4 in dilute H2SO4
    (decolourisation of purple KMNO4 solution)
42
Q

why is phenol the most acidic amongst water and ethanol?

A

in phenoxide ion, the lone pair of electrons on the oxygen atom is delocalised into the benzene ring that results in the dispersal of the negative charge on the phenoxide ion, hence stabilising the phenoxide ion.

43
Q

phenol to phenoxide

A
  1. reactive metal (eg. Na and K) to form O-Na+

2. NaOH (aq) (neutralisation)

44
Q

phenol does not react with carboxylic acid because ________

A

phenol is a weaker nucleophile than an alcohol since the lone pair of electrons on the O atom is delocalised into the benzene ring.

45
Q

phenol to ester

A

ROCl (nucleophilic acyl substitution)

46
Q

phenol more susceptible to ES compared to benzene because ________

A

in phenol, the lone pair of the electrons on O atom is delocalised into the benzene ring thereby increasing the electron density in the ring, hence increasing reactivity towards ES

47
Q

phenol to 2-nitrophenol or 4-nitrophenol

A

HNO3 (aq), rtp

48
Q

phenol to 2,4,6-trinitrophenol

A

conc HNO3

49
Q

test for phenol

A
  1. Br2 (aq)
    (decolourisation of orange Br2 (aq) and formation of white 2,4,6-tribromophenol)
  2. neutral FeCl3 (aq)
    (violet complex observed)
50
Q

Nucleophilic Addition product: hydroxynitrile

A

HCN with trace amounts of NaOH as catalyst, cold

51
Q

test for carbonyl compounds

A

2,4-DNPH, heat

orange ppt

52
Q

test to distinguish ketone and aldehyde

A

Tollens’ reagent, heat

aldehyde: silver mirror

53
Q

test to distinguish aliphatic and aromatic aldehyde

A

Fehling’s reagent, heat

aliphatic: brick red ppt

54
Q

iodoform test for RCOCH3

to form RCOO-Na+ +CHI3 + 3NaI + 3H2O

A

alkaline I2(aq)

55
Q

concept about acidity

A

strength of acid depends on the stability of the conjugate base

the more dispersed the negative charge on the carboxylate anion, the more stable the conjugate base and hence stronger acid

56
Q

carboxylic acid is stronger than alcohols and phenols because ______

A

the carboxylate (COO-) is resonance stabilised by the delocalisation of the negative charge over the C atom and both electronegative O atoms in the anion.

The intensity of the negative charge on the anion is less than that of the phenoxide or alkoxide ion, hence anion more stable.

57
Q

carboxylic acid to pri alcohol

A

LiAlH4 in dry ether

58
Q

RCOOH to RCOO-Na+

A

reactive metals (eg. Na , Mg, Ca)

59
Q

RCOOH to RCOO- part 2

A

NaOH(aq) / KOH(aq) / Ca(OH)2 (aq)

60
Q

RCOOH to 2RCOO-Na+

A

Na2CO3 (aq)/(s)

61
Q

RCOOH to RCOO-Na+ pt 3 of carbonates

A

NaHCO3 (aq)/(s)

62
Q

esterification of COOH with OH

A

RCOOH and OH to form COO

conc H2SO4 as catalyst, heat

63
Q

RCOOH to RCOCl

A
  1. anhydrous PCl5
  2. anhydrous PCl3
  3. anhydrous SOCl2
64
Q

HCOOH oxidised to give _______

methanoic acid

A

CO2 and H2O

KMNO4 or K2CrO7, dilute H2SO4, heat

65
Q

(COOH)2 oxidised to give ______

ethanedioic acid

A

2CO2 + H2O

KMNO4 in dilute H2SO4. heat

NO K2CRO7!!!

66
Q

test for COOH

A
  1. add NaCO3
    (effervescence of CO2 that forms white ppt with Ca(OH)2)
  2. anhydrous PCl5
    (white fumes of HCl)
67
Q

ester to COOH

A

H2SO4(aq) / HCl (aq), heat under reflux

68
Q

ester to RCOO-Na+

A

NaOH(aq), heat under reflux

69
Q

amines have higher bp than hydrocarbons with same Mr due to ________

A

stronger intermolecular hydrogen bonding

70
Q

amines have lower mp than alcohol of similar Mr due to _________

A

intermolecular hydrogen bonding in amines being weaker than those in alcohol since the N-H bond is less polar than O-H bond

71
Q

pri amide to pri amine

A

LiAlH4 in dry ether

72
Q

nitrobenzene to phenylamine

A

Sn in excess conc HCl and heat
followed by NaOH(aq)

(REDUCTION AND IMPORTANT!!!)

73
Q

ethylamine is a stronger base than ammonia because ________

A

electron donating alkyl group increases the electron density of the lone pair on N atom, hence lone pair on N atom is more available to accept a proton.

74
Q

relative basicity of aliphatic amines in gaseous phase

NH2(CH3) vs NH(CH3)2 vs N(CH3)3

A

most basic tri>di>methylamine

increase in no. of alkyl groups increases the electron density of the lone pair on N atom, hence lone pair on N atom is more available to form A DATIVE BOND.

75
Q

R-NH2 to R-NH3+

A

HCl (aq) or H2SO4 (aq)

76
Q

amine to amide

A

anhydrous RCOCl (condensation)

77
Q

phenylamine to 2,4,6-tribromophenylamine

A

Br2 (aq) (ES)

(decolourisation of orange Br2 solution with the formation of white ppt

78
Q

why are the conditions required to form 2,4,6-tribromophenylamine from phenylamine mild? (no catalyst required)

A

phenylamine is more reactive then benzene towards ES as the -NH2 group activates the ring towards ES. This is due to lone pair on N atom being delocalised into the benzene ring hence increasing electron density in the ring

79
Q

amides are neutral and no basic because__________

A

the lone pair on N atom is delocalised into the pi bond of the adjacent C O double bond hence reducing the electron density on the N atom, lone pair on N atom is less available to accept a proton

80
Q

amides to RCOOH and NH4+

A

HCl (aq) / H2SO4 (aq), heat under reflux

81
Q

amides to RCOO-Na+ and NH3

A

NaOH(aq), heat under reflux

PUNGENT NH3 CONFIRMS AMIDE IS PRIMARY

82
Q

test for amides , NH4+X and amine

A

NaOH(aq)

turn moist red litmus paper blue as NH3 gas is produced

chem organic reactions (1 decks)

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