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Chemistry OCR A > Organic reactions > Flashcards

Organic reactions Flashcards

1
Q

Conditions to turn primary alcohol into an aldehyde

A

Distillation and use of oxidising agent like Acidified potassium dichromate (vii)

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2
Q

How to turn primary alcohol into a carboxylic acid?

A

Heat under reflux and add oxidising agent of acidified potassium dichromate (vii)

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3
Q

How to turn secondary alcohols into ketones?

A

Heat under reflux with oxidising agent like acidified potassium dichromate (vii)

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4
Q

Colour change for reduction of dichromate (vii) ions?

A

orange to green

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5
Q

Conditions of oxidising for tertiary alcohols?

A

They do not oxidise under normal conditions

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6
Q

How to dehydrate alcohols to alkenes?

A

Heat under reflux and add concentrated phosphoric acid

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7
Q

How to go from alcohols to haloalkanes?

A

Heat under reflux with concentrated sulphuric acid

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8
Q

How to go from alkenes to alcohols?

A

Steam and phosphoric acid (electrophilic addition)

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9
Q

How to go from an alkene to a haloalkane?

A

Room temp
Hydrogen halides in a gaseous state
(Electrophilic addition)

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10
Q

How to go from alkene to an alkane?

A

Nickel catalyst
423 Kelvin
(Electrophilic addition)

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11
Q

How to go from alkane to haloalkane?

A

UV Light
(Free radical substitution)

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12
Q

Conditions of the nitration of Benzene?

A

Electrophilic substitution
Conc. HNO₃ and Conc. H₂SO₄ catalyst
50°C for mono nitration

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13
Q

Conditions of halogenation of benzene?

A

Electrophilic substitution (Cl ⁺ or Br ⁺ )
Halogen (e.g.Cl₂) + Halogen Carrier catalyst (e.g. AlCl₃/FeCl₃)

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14
Q

Benzene reacting with haloalkanes conditions

A

Electrophilic substitution ( CH₃⁺) = alkylation
Halogen carrier catalyst + reflux +anhydrous conditions
Friedel-Crafts reaction

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15
Q

Benzene reacting with acyl chlorides conditions

A

Electrophilic substitution (CH₃C⁺O) = acylation
Halogen carrier catalyst + reflux + anhydrous conditions
Friedel-Crafts reactions

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16
Q

Phenol reacting with Nitric acid conditions

A

Electrophilic substitution
dilute HNO₃, no catalyst (reacts much more readily than benzene)
forms 2 isomers: 2-nitrophenol and 4-nitrophenol

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17
Q

Phenol reacting with bromine conditions

A

Electrophilic substitution
no catalyst + decolourises orange bromine
product = 2,4,6-tribromophenol =antiseptic

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18
Q

Reactions of phenol and NaOH

A

Neutralisation reaction
Phenol = weak acid: not acidic enough to react with carbonates :(

19
Q

How to go from aldehydes to primary alcohols?

A

Nucleophilic addition (H⁻ Hydride ions)
Reducing agent = NaBH₄ (supplies hydride ions)
Add water)

20
Q

How to go from a ketone to a secondary alcohol?

A

Nucleophilic addition (H⁻ hydride ions)
Reducing agent = NaBH₄ (supplies hydride ions)
Then add water)

21
Q

Reactions of carbonyls and hydrogen cyanide (description, benefit)

A

Nucleophilic addition (:CN⁻⁻⁻)
HCN = weak acid, partially dissociates in water ⟶ CN⁻⁻⁻
CN⁻⁻⁻ attacks δ+ carbon on carbonyl group
Extends carbon chain
H⁺ (from H₂O or HCN) bonds to oxygen = hydroxyl group

22
Q

How to go from carboxylic acid to acyl chloride?

A

React with SOCl₂ = thionyl chloride
OH group replaced by Cl group

23
Q

How to go from acyl chloride to an ester?

A

React with an alcohol, faster and easier than by using a carboxylic acid and an alcohol

24
Q

How to go from a carboxylic acid to an ester?

A

Add alcohol
Heat with acid catalysts (H₂SO₄)
Reversible reaction: separate product as it forms using fractional distillation
N.B Oxygen in ester bonds comes from alcohol

25
Q

How to go from an ester back to a carboxylic acid?

A

Add water
Acid hydrolysis
Reflux ester with hot quests acid e.g. HCl, H₂SO₄ (dilute)

26
Q

How to get an alcohol and a salt from an ester?

A

react with an alkali
Base hydrolysis
reflux ester with a hot aqueous alkali e.g. NaOH (dilute)

27
Q

How to get phenylamine from nitrobenzene?

A

Heating under reflux with tin catalysts + conc. HCl
if 2 substitutions: 12[H] and 4H₂O !!
Must add NaOH (phenyl amine +HCl ⟶ salt :( )
Reduction

28
Q

Amino Acid + Acid ⟶

A

Amino Acid + Acid ⟶ Salt

If pH is lower than isoelectric point, amino acid behaves as a base: amino group reacts
NH₂ ⟶ NH₃⁺ = cation

29
Q

Amino Acid + Base ⟶

A

Amino Acid + Base ⟶ Salt + Water

If pH is higher than isoelectric point, amino acid behaves as an acid: COOH group reacts
COOH ⟶ COO⁻⁻⁻ = anion

30
Q

Amino acid + Alcohol ⟶

A

Amino acid + Alcohol ⟶ Ester + water

Strong acid catalyst (H₂SO₄)

31
Q

Amino Acid + Amino Acid ⟶

A

Amino Acid + Amino Acid ⟶ Amide (dipeptide)

Condensation reaction: elimination of H₂O
Forms a dipeptide = secondary amide

32
Q

Dicarboxylic acid + Diamine ⟶

A

Dicarboxylic acid + Diamine ⟶ Polyamide + water

Condensation polymer (loses H₂O)

33
Q

Dicarboxylic acid + Diol ⟶

A

Dicarboxylic acid + Diol ⟶ Polyester + water

Condensation polymer (loses H₂O)

34
Q

H⁺

Polyamide + 2H₂O ⟶

A

H⁺
Polyamide + 2H₂O ⟶ Dicarboxylix acid + diamine

Polyamide hydrolyses more easily with an acid than a base = acid hydrolysis

35
Q

Polyester + 2NaOH ⟶

A

Polyester + 2NaOH ⟶ Dicarboxylix acid salt + Diol

Polyesters hydrolysis more easily with a base than an acid = base hydrolysis

36
Q

Haloalkane + CN⁻⁻⁻ ⟶

A

Haloalkane + CN⁻⁻⁻ ⟶ Nitrile + X⁻⁻⁻

Nucleophilic substitution
Reflux haloalkane with potassium cyanide in ETHANOL SOLVENT

37
Q

Nitrile + 4[H] ⟶

A

Nitrile + 4[H] ⟶ Primary amine

Reduction (method 1)
Use Lithium Aluminium Hydride: LiAlH₄, which is a strong reducing agent, and dilute acid

38
Q

Nitrile + 2H₂ (g) ⟶

A

Nitrile + 2H₂ (g) ⟶ Primary amine

Reduction (method 2 - used in industry)
Hydrogen gas, metal catalyst (e.g. Platinum or Nickel)
High temp + pressure

N.B Nitriles can also be reduced with sodium metal and ethanol !!

39
Q

Nitrile + 2H₂O + HCl ⟶

A

Nitrile + 2H₂O + HCl ⟶ Carboxylic acid + NH₄Cl

Acid hydrolysis
reflux nitrile in dilute HCl (with heat)

40
Q

Haber Process

A

N₂ (g) + 3H₂ (g) ⇌ 2NH₃ (g)

Forward reaction = exothermic
High pressure favours forward reaction

BUT
low temp decreases yield so compromise @ 450°C
High pressure = dangerous & expensive compromise of 200 atm.
Finely divided porous iron catalyst

41
Q

Acyl chloride + alcohol =

A

ester + HCl

42
Q

Acyl chloride + Phenol

A

ester +HCl

43
Q

Acyl chloride + Water

A

Carboxylic acid + HCl

44
Q

Acyl chloride + Ammonia/amines

A

Amide + NH4Cl (ammonia chloride)

Chemistry OCR A (12 decks)

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