⚫️ Organic Chemistry - Mechanisms Flashcards

1
Q

How would you make an alkane from an alkene?

A

Reagent: H2
Condition: nickel catalyst (heterogenous) + heat (200C)
Type of reaction: electrophilic addition

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2
Q

How would you make an alcohol from an alkene?

A

Reagent: H3PO4 + H2O(g) [steam]
Condition: warm
Type of reaction: electrophilic addition

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3
Q

How would you make a diol from an alkene?

A

Reagent: acidified potassium manganate (VII)
Condition: room temp.
Type of reaction: electrophilic addition

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4
Q

How would you make a halogenoalkane from an alkene?

A

Reagent: HX
Condition: room temp.
Type of reaction: electrophilic addition

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5
Q

How would you make a dihalogenoalkane from an alkene?

A

Reagent: X2
Condition: room temp.
Type of reaction: electrophilic addition

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6
Q

How would you make an alkene from an alkane?

A

Reagent: -
Condition: high temp. + catalyst (Al2O3)
Type of reaction: cracking

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7
Q

How would you make a halogenoalkane from an alkane?

A

Reagent: X2
Condition: UV
Type of reaction: free radical substitution

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8
Q

What are the three different types of halogenoalkane that can be made from an alcohol?

A
  1. Chlorohalogenoalkane (chlorination)
  2. Bromohalogenoalkane (bromination)
  3. Iodohalogenoalkane (iodination)
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9
Q

How would you make a chlorohalogenoalkane from an alcohol?

A

Reagent: PCl5 (/conc. HCl for tertiary)
Condition: room temp.
Type of reaction: nucleophilic substitution/ halogenation/ chlorination

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10
Q

How would you make a bromohalogenoalkane from an alcohol?

A

Reagent: KBr + conc.H2SO4 (to make HBr)
Condition: reflux
Type of reaction: nucleophilic substitution/ halogenation/bromination

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11
Q

How would you make an iodohalogenoalkane from an alcohol?

A

Reagent: (red) P + I2 (to make PI3)
Condition: reflux
Type of reaction: nucleophilic substitution/ halogenation/ iodination

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12
Q

How would you make an alkene from a halogenoalkane?

A

Reagent: ethanolic KOH
Condition: heat
Type of reaction: elimination

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13
Q

How would you make an alcohol from a halogenoalkane?

A

Reagent: H2O or AQUEOUS alkali (OH-)
Condition: heat
Type of reaction: nucleophilic substitution

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14
Q

How would you make a nitrile from a halogenoalkane?

A

Reagent: KCN (:CN-)
Condition: reflux
Type of reaction: nucleophilic substitution

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15
Q

How would you make a primary amine from a halogenoalkane?

A

Reagent: excess NH3 (:NH3) in ethanol [ethanolic to dissolve the halogenoalkane]
Condition: heat in sealed tube (heated to increase rate of reaction, sealed to prevent excess ammonia gas escaping), (high pressure)
Type of reaction: nucleophilic substitution

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16
Q

How would you make a ketone from an alcohol? What would be made as a by-product?

A

From: secondary alcohol
Reagent: K2Cr2O7 + H2SO4 [O] (potassium dichromate)
Condition: heat/ reflux
Type of reaction: oxidation
By-product made: water

17
Q

How would you make an aldehyde from an alcohol? What is the by-product made?

A

From: primary alcohol
Reagent: K2Cr2O7 + H2SO4 [O] (ACIDIFIED potassium dichromate)
Condition: heat - DISTILLATION (as opposed to reflux)
Type of reaction: oxidation
By-product made: water

18
Q

How would you make a carboxylic acid from an alcohol? What is the by-product made?

A

From: primary alcohol (/aldehyde)
Reagent: K2Cr2O7 + H2SO4 [O] (potassium dichromate)
Condition: reflux
Type of reaction: oxidation
By-product made: water

19
Q

How would you make an alkene from an alcohol? What is the by-product made?

A

Reagent: concentrated phosphoric acid (H3PO4)
Condition: heat
Type of reaction: elimination (dehydration)
By-product made: water

20
Q

How would you make a primary amine from a nitrile?

A

Reagent: LiH4Al (lithium tetrahydridoaluminate) in dry ether [H] - (but this is referring only to 1 hydrogen NOT the four in LiH4Al)
Condition: anhydrous conditions
Type of reaction: reduction

21
Q

How would you make a carboxylic acid from a nitrile/hydroxynitrile? What are the by-products made?

A

Reagent: dilute acid OR aqueous alkali (+dilute acid)
Condition: heat under reflux
Type of reaction: hydrolysis
By-products made: NH4+ (if acid hydrolysis) or NH3 (if alkaline hydrolysis)

22
Q

How would you make an alcohol from a ketone?

A

Reagent: LiH4Al (lithium tetrahydridoaluminate) in dry ether [H]
Condition:
Type of reaction: reduction
Product: secondary alcohol

23
Q

How would you make an alcohol from an aldehyde/carboxylic acid?

A

Reagent: LiH4Al (lithium tetrahydridoaluminate) [H] in dry ether
Condition:
Type of reaction: reduction
Product: primary alcohol only (the carboxylic acid will reduce straight to the alcohol and NOT to an aldehyde first)

24
Q

How would you make a hydroxynitrile from a carbonyl compound?

A

From: aldehyde/ketone
Reagent: HCN in presence of KCN
Condition: reflux
Type of reaction: nucleophilic ADDition

25
Q

How would you make an acyl chloride from a carboxylic acid?

A

Reagent: PCl5
Condition: anhydrous conditions, room temperature
Type of reaction: halogenation

26
Q

How would you make a carboxylate salt from a carboxylic acid?

A

Reagent: aqueous alkali (base)
Condition:
Type of reaction: neutralisation

27
Q

How would you make an ester from a carboxylic acid?

A

Reagent: an alcohol (the length chain of the alcohol depends on the carbon chain bonded to the -O- in the ester)
Condition: acid catalyst + heat
Type of reaction: esterification (reverse of hydrolysis of an ester to a carboxylic acid) - lies in an equilibrium

28
Q

How would you make a carboxylic acid from an ester? What is the by-product made?

A

Reagent: H2O
Condition: acid catalyst + warm
Type of reaction: (acid) hydrolysis (reverse of esterification of a carboxylic acid) - lies in an equilibrium
By product: alcohol

29
Q

How would you make an ester from an acyl chloride?

A

Reagent: an alcohol (the length chain of the alcohol depends on the carbon chain bonded to the -O- in the ester)
Condition: room temp
Type of reaction: esterification

30
Q

How would you make a primary amide from an acyl chloride?

A

Reagent: conc. ammonia solution
Condition: room temp.
Type of reaction:

31
Q

How would you make N-substituted amides from an acyl chloride? What would you see?

A

Reagent: for 2 amide - 1 amine, for 3 amide - 2 amine
Condition: room temp.
Type of reaction:
Observation: steamy white fumes (HCl)

32
Q

How would you make 2 amine, 3 amine, quaternary ammonium salt from a halogenoalkane?

A

Reagent: for 2 amine - 1 amine, for 3 amine - 2 amine, for quaternary ammonium salt - 3 amine
(Therefore excess halogenoalkane will go to a quaternary ammonium salt)
Condition:
Type of reaction: nucleophilic substitution

33
Q

How would you make a carboxylate salt from an ester? How can this be made into a more useful product? What is the by-product?

A

Reagent: alkali (OH-)
Condition:
Type of reaction: hydrolysis in alkaline solution (base hydrolysis)
By product: alcohol
Carboxylate salt can be converted into a carboxylic acid by adding a dilute acid (H+)

34
Q

How would you make a carboxylic acid from an acyl chloride?

A

Reagent: (cold) water
Conditions: room temp.
Type of reaction: