Organic Reactions Flashcards

(55 cards)

1
Q

conditions for the reduction of an alkene to an alkane

A

nickel catalyst
H2
150°C

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2
Q

conditions for the oxidation of an alkene to a diol

A

KMno4 (aq)
H2SO4 (aq)
goes from purple to colourless

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3
Q

conditions for polymerisation

A

heat and pressure

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4
Q

conditions for the electrophilic addition of an OH from an alkene to an alcohol

A

H2O gas
H3PO4
300°C
60-70 atm

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5
Q

conditions for the elimination of H2O from an alcohol to an alkene

A

heat

H3PO4 (conc)

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6
Q

conditions for the addition of a halogen to an alkene to make a halogenoalkane

A

Hydrogen halide

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7
Q

conditions for the elimination of a halogen from a halogenoalkane to an alkene

A

KOH (ethanol)

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8
Q

conditions for the substitution of an OH with chlorine (from alcohol to chloroalkane)

A

PCl5 or conc. HCl

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9
Q

conditions for the substitution of an OH with iodine (from alcohol to iodoalkane)

A

red phosphorus

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10
Q

conditions for the substitution of an OH with bromine

A

KBr and conc. H2SO4

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11
Q

conditions for the partial oxidation of a primary alcohol and what does it make?

A

makes aldehyde
limited [O] - K2Cr2O7
dilute H2SO4
distill out aldehyde, as it has lowest boiling point

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12
Q

conditions for the full oxidation of a primary alcohol and what does it make?

A

makes a carboxyllic acid
excess [O] - K2Cr2O7
dilute H2SO4
heat under reflux

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13
Q

conditions for the oxidation of a secondary alcohol and what does it make?

A

makes ketone
K2Cr2O7
H2SO4
heat under reflux and then distill

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14
Q

alkene to dihalogenoalkane

A

electrophilic addition of halogen

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15
Q

alkene to halogenoalkane

A

electrophilic addition of hydrogen halide

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16
Q

test for alkenes

A

shake with bromine water, goes from orange to colourless

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17
Q

how to make a chloroalkane

A
  • alcohol
  • PCl5
  • produces HCl and POCl3
  • fizzing and steamy white fumes
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18
Q

how to make a bromoalkane

A
  • 50% H2SO4 + NaBr –> HBr + NaHSO4
  • alcohol + HBr –> bromoalkane + H2O
  • H2SO4 is 50% concentrated so it is low enough to prevent it oxidising HBr to bromine
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19
Q

how to make an iodoalkane

A
  • red phosphorus
  • P + I2 –> PI3
  • alcohol + PI3 –> iodoalkane + H3PO3
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20
Q

aldehyde / ketone to alcohol

A
  • reduction
  • nucleophilic addition of LiAlH4
  • add LiAlH4 in dry ether
  • R-CHO + 2[H] –> R-OH
  • R-CO-R + 2[H] –> R-OH-R
  • after the reduction you add HCl (aq) to hydrolyse the leftover LiAlH4
  • check mechanism
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21
Q

iodoform test

A
  • tests for methylketones, ethanal and secondary alcohols

- gives pale yellow precipitate with antiseptic smell

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22
Q

2,4-DNPH test

A
  • tests for aldehydes and ketones
  • forms yellow/orange ppt
  • can identify compound by filtering ppt, purifying by recrystallisation, measure melting point and compare to known data
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23
Q

Tollens’ Reagent

A
  • tests for aldehydes
  • alkaline solution of Ag+
  • forms silver mirror on test tube
24
Q

Fehling’s / Benedict’s Solution

A
  • tests for aldehydes
  • alkaline solution of Cu2+
  • blue solution to red precipitate
25
aldehyde to carboxylic acid
- acidic oxidation - add acidified potassium dichromate (VI) K2Cr2O7 - orange solution to green solution
26
carboxylic acid to alcohol
- reduction - LiAlH4 in dry ether - goes from carboxylic acid --> aldehyde --> alcohol
27
carboxylic acid + PCl5
acyl chloride + POCl3
28
how to make an acyl chloride
- carboxylic acid + PCl5 | - also makes POCl3
29
write out equation for ethanoic acid + NaOH
check
30
write out equation for ethanoic acid + Ca2O
check
31
slow way to make an ester
- carboxylic acid + alcohol --> ester + H2O - needs concentrated H2SO4 catalyst so slow - reversible so incomplete and low yield
32
fast way to make an ester
- acyl chloride + alcohol --> ester + HCl | - fast and complete reaction
33
acidic hydrolysis of an ester
- ester + H2O --> alcohol + carboxylic acid - slow as it needs dilute H2SO4 catalyst - incomplete so low yield
34
alkaline hydrolysis of an ester
- ester + NaOH --> salt + alcohol - add HCl to turn salt into carboxylic acid - fast and complete reaction
35
how to make a polyester
condensation reaction with an alcohol and carboxylic acid, each with 2 functional groups on each
36
reaction of benzene with oxygen in air
combustion, gives a very sooty flame as the C:H ratio is very high
37
bromination of benzene mechanism
- check mechanism - AlBr3 catalyst - eventually goes from orange to colourless
38
how to make nitrobenzene
- HNO3 conc. and H2SO4 conc. - check mechanism - T < 50°C prevents too many substitutions and TNT is explosive
39
mechanism of Friedel-Crafts alkylation
- check mechanism | - bromoalkane and AlBr3 catalyst
40
mechanism of Friedel-Crafts acylation
- check mechanism | - acyl chloride and AlCl3 catalyst
41
mechanism of bromination of phenol
- check mechanism | - solid product as it's a large molecule and breaks more hydrogen bonds than it makes
42
bad way to make an amine
R - Br + NH3 --> R-NH2 + HBr - nucleophilic substitution - check mechanism - can't prevent multiple substitutions
43
good way to make an amine
- reduction of a nitrile | - LiAlH4 in dry ether
44
reduction of nitrobenzene with equations
- conc, HCl (aq) - Sn - heat under reflux - add NaOH - check equation
45
amine + water equation
- forms alkaline solution - reversible reaction - NH2 part + H+ --> NH3+ group
46
amine + HCl
check salt
47
amine + water
check salt
48
amine + propanoic acid
check salt
49
how to make an amide
amine + acyl chloride --> amide + HCl
50
amine + halogenoalkane
check reaction
51
formation of polyamides
- condensation polymerisation | - always release HCl or H2O
52
draw repeat unit of dicarboxylic acid and diamine
check
53
draw repeat unit of diacyl chloride and diamine
check
54
draw repeat unit of amino acid polyamide
- check | - form peptide bond
55
hydrolysis of peptide bond (draw)
- heat under reflux - HCl (aq) or NaOH(aq) and water - amino acids produced which can be separated by chromotography - check products with HCl and NaOH