T7: Haloalkanes Flashcards

1
Q

how are haloalkanes formed

A

by reacting an alkane with a halogen

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2
Q

name of the mechanism of how haloalkanes are formed

A

free-radical substitution

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3
Q

one essential condition for free-radical substitution

A

UV light

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4
Q

why is UV light essential for free-radical substitution

A

provides energy required to break the halogen-halogen bond and start the reaction

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5
Q

free radical definition

A

a species with an unpaired electron

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6
Q

3 stages of free-radical substitution

A

Initiation
Propagation 1
Propagation 2
Termination

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7
Q

initiation (reaction between methane and chlorine)

A

Cl2 -> 2Cl·

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8
Q

propagation 1 (reaction between methane and chlorine)

A

Cl· + CH4 -> ·CH3 + HCl

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9
Q

propagation 2 (reaction between methane and chlorine)

A

·CH3 + Cl2 -> CH3Cl + Cl·

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10
Q

how many possibilities are there in the termination stage

A

3

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11
Q

termination (reaction between methane and chlorine)

A

·CH3 + ·CH3 -> C2H6
·Cl + ·Cl -> Cl2
·CH3 + ·Cl -> CH3Cl

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12
Q

description of termination

A

2 free radicals combine

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13
Q

name of the mechanism when another halogen molecule reacts again by free-radical substitution

A

further substitution

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14
Q

initiation (reaction between chloromethane and chlorine)

A

Cl2 -> 2Cl·

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15
Q

propagation 1 (reaction between chloromethane and chlorine)

A

Cl· + CH3Cl -> ·CH2Cl + HCl

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16
Q

propagation 2 (reaction between chloromethane and chlorine)

A

·CH2Cl + Cl2 -> CH2Cl2 + Cl·

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17
Q

termination (reaction between chloromethane and chlorine)

A

·CH2Cl + ·CH2Cl -> C2H4Cl2
·Cl + ·Cl -> Cl2
·CH2Cl + ·Cl -> CH2Cl2

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18
Q

to reduce the amount of further substitution you would

A

use excess haloalkane

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19
Q

what are curly arrows used to show

A

show the movement of a pair of electrons

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20
Q

rules for curly arrows -> must start from:

A
  • a lone pair of electrons
  • covalent bond
21
Q

rules for curly arrows -> must go to:

A
  • partially positive / positive atom
  • somewhere a bond is being formed
22
Q

nucleophile definition

A

electron pair donor

23
Q

3 different nucleophiles that react with haloalkanes

A

:OH-
:C-N
:NH3

24
Q

what do substitution reactions always involve

A

one group / atom replacing another group / atom in a molecule

25
Q

nucleophilic substitution by OH- ions -> reagent?

A

NaOH or KOH

26
Q

nucleophilic substitution by OH- ions -> conditions?

A

Aqueous solvent

27
Q

nucleophilic substitution by OH- ions -> type of product?

28
Q

nucleophilic substitution by OH- ions -> what is the nucleophile in this reaction?

29
Q

nucleophilic substitution by OH- ions -> this reaction is a substitution reaction because…?

A

OH substitutes for Br

30
Q

nucleophilic substitution by OH- ions -> overall reaction?

A

CH3CH2Br + NaOH -> CH3CH2OH + NaBr

31
Q

nucleophilic substitution by C-N ions -> reagent?

32
Q

nucleophilic substitution by C-N ions -> conditions?

A

Aqueous + ethanol solvent

33
Q

nucleophilic substitution by C-N ions -> type of product?

34
Q

nucleophilic substitution by C-N ions -> what is the nucleophile in this reaction?

35
Q

nucleophilic substitution by C-N ions -> this reaction is a substitution reaction because…?

A

CN swapping for Br

36
Q

nucleophilic substitution by C-N ions -> overall reaction?

A

CH3CH2Br + KCN -> CH3CH2CN + KBr

37
Q

nucleophilic substitution by NH3 ions -> reagent?

A

excess ammonia

38
Q

nucleophilic substitution by NH3 ions -> conditions?

A

ethanol solvent, heat and pressure

39
Q

nucleophilic substitution by NH3 ions -> type of product?

40
Q

nucleophilic substitution by NH3 ions -> what is the nucleophile in this reaction?

41
Q

nucleophilic substitution by NH3 ions -> this reaction is a substitution reaction because…?

A

a Br atom has been swapped for an NH2 group

42
Q

nucleophilic substitution by NH3 ions -> overall reaction(s)?

A

C2H5Br + NH3 -> C2H5NH2 + HBr

C2H5Br + 2NH3 -> C2H5NH2 + NH4Br

43
Q

elimination -> reagent?

A

NaOH or KOH

44
Q

elimination -> conditions?

A

Ethanolic solvent (alcoholic)

45
Q

elimination -> type of product?

46
Q

elimination -> in this reaction the OH- ion acts as a…?

A

base (proton acceptor)

47
Q

elimination -> this reaction is a elimination reaction because…?

A

A H atom and a Br atom have been removed from the reactant molecule

48
Q

elimination -> overall reaction?

A

CH3CHBrCH3 + NaOH -> CH2=CHCH3 + NaBr + H2O