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Halogenoalkanes Flashcards

1
Q

Halogenoalkanes:

What’s meant by Halogenoalkanes?

A

When H in Alkanes are replaced w Halogens

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2
Q

Halogenoalkanes:

What are Halogenoalkanes reacted with?

A

Nucleophiles

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3
Q

Halogenoalkanes:

What are Nucleophiles?

A

Species that donate electron pairs

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4
Q

Halogenoalkanes:

What charge are Nucleophiles?

A

δ- or -

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5
Q

Halogenoalkanes: Primary,Secondary & Tertiary Structures

What are Primary Halogenoalkanes?

Carbon-cation is found by breaking Halogen away from C

A

Carbon-cation is attached to 1 Alkyl Group & 2 Hydrogens

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6
Q

Halogenoalkanes: Primary,Secondary & Tertiary Structures

What are Secondary Halogenoalkanes?

Carbon-cation is found by breaking Halogen away from C

A

Carbon-cation is attached to 2 Alkyl Groups & 1 Hydrogen

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7
Q

Halogenoalkanes: Primary,Secondary & Tertiary Structures

What are Tertiary Halogenoalkanes?

Carbon-cation is found by breaking Halogen away from C

A

Carbon-cation is attached to 3 Alkyl Groups & no Hydrogens

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8
Q

Halogenoalkanes: Primary,Secondary & Tertiary Structures

Which Halogenoalkanane Structure is most stable?

A

Tertiary

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9
Q

Halogenoalkanes: Bond Enthalpy

How do you break Halogenoalkane?

A

Break halogen away from Carbon chain attaching the chain to something else

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10
Q

Halogenoalkanes: Bond Enthalpy in terms of IMFs

What’s the trend of Halogenoalkanes in terms of Bond Enthalpy & IMFs?

A
  • Down G7, atomic radius increases
    ↳ more electrons
    ↳ more IMFs
    ↳ higher mp/bp : more energy needed to break it down

Hence C-I has the highest mp/bp
↳ hardest to break

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11
Q

Halogenoalkanes: Bond Enthalpy in terms of NC

What’s the trend of Halogenoalkanes in terms of Bond Enthalpy & NC?

A
  • Down G7, atomic radius increases
    ↳ outer e- = further away shielded by inner e-
    ↳ ionise quicker : nuclear charge is reduced
    ↳ lower mp/bp : less energy needed to break it down

Hence C-I has the lowerst mp/bp
↳ easiest to break

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12
Q

Halogenoalkanes: Bond Enthalpy IMFs VS NC

Which one takes priority?

A

Nuclear Charge

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13
Q

Halogenoalkanes: Bond Enthalpy IMFs VS NC

Why does NC take priority?

A

Weaker Carbon-Hydrogen (e.g C-I) bonds break first
↳ they react the fastest

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14
Q

Halogenoalkanes: Halogenoalkane Hydrolysis using Water

What’s formed when a Halogenoalkane is hydrolysed w water?

A

An alcohol

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15
Q

Halogenoalkanes: Halogenoalkane Hydrolysis using Water

What’s the equation for this reaction?

A
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16
Q

Halogenoalkanes: Halogenoalkane Hydrolysis using Water

What type of Fission occurs?

A

Heterolytic Fission
↳ bond breaks unevenly, an atom receives both radicals forming 2 ions

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17
Q

Halogenoalkanes: Halogenoalkane Hydrolysis using Water

What’s the Nucleophile in this reaction?

A

Water

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18
Q

Halogenoalkanes: Halogenoalkane Hydrolysis using Water

How would you identify the Halide formed in this reaction?

A

Add Silver Nitrate into solution

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19
Q

Halogenoalkanes: Halogenoalkane Hydrolysis using Water

Why would you add Silver Nitrate to the solution?

A

Silver Halide precipitate is formed at different rates
↳ undissolved solid

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20
Q

Halogenoalkanes: Halogenoalkane Hydrolysis using Water

How would you identify the Halide?

A

Identify colour change

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21
Q

Halogenoalkanes: Halogenoalkane Hydrolysis using Water

What colour is the AgCl Precipitate?

A

White

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22
Q

Halogenoalkanes: Halogenoalkane Hydrolysis using Water

What colour is the AgBr Precipitate?

A

Cream

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23
Q

Halogenoalkanes: Halogenoalkane Hydrolysis using Water

What colour is the AgI Precipitate?

A

Pale Yellow

24
Q

Halogenoalkanes: Primary,Secondary & Tertiary have diff reactivities

What’s the relationship between the Type of Structure the Halogenoalkane forms & Reactivity?

A
  • Down the table, the faster the Halogenoalkane is broken
    ↳ more Alkyl groups = more stable
    ↳ more reactive it is : quicker it breaks
25
# **Halogenoalkanes:** Nucleophiles What are 4 examples of Nucleophiles?
* Hydroxide (OH-) * Water (H2O) * Ammonia (NH3) * Cyanide Ions (CN-)
26
# **Halogenoalkanes:** Nucleophiles What is considered a Nuclophile?
Anything with a lone pair of e- ↳ H2O & NH3 are neutral nucleophiles
27
# **Halogenoalkanes:** Nucleophillic Substitution What occurs in this Reactions?
Nuc replaces X
28
# **Halogenoalkanes:** Nucleophillic Substitution What does a Nucleophillic Substitution mechanism look like?
29
# **Halogenoalkanes:** Nucleophillic Substitution What does the 'Nuc' represent?
Nucleophile
30
# **Halogenoalkanes:** Nucleophillic Substitution What does the 'X' represent?
Halogen
31
# **Halogenoalkanes:** Nuclophillic Substitution What's Nucleophillic Substitution?
When halogenoalkanes are hydrolysed to alcohols
32
# **Halogenoalkanes:** Nucleophillic Substitution What's the 1st Step of Nucleophillic Substitution?
Nuc provides a pair of electrons to the C (δ+)
33
# **Halogenoalkanes:** Nucleophillic Substitution What's the 2nd Step of Nucleophillic Substitution?
C-X bond breaks heterolytically ↳ bond breaks unevenly, a species gains both electrons (Halogen) forming 2 ions
34
# **Halogenoalkanes:** Nucleophillic Substitution What's the 3rd Step of Nucleophillic Substitution?
* Nuc bonds to C * Halogen takes both electrons
35
# **Halogenoalkanes:** Forming Alcohols What do Halogenoalkanes react w to form an Alcohol?
Aqueous KOH ↳ provides OH- group
36
# **Halogenoalkanes:** Forming Alcohols What's the Equation for this Reaction?
37
# **Halogenoalkanes:** Forming Alcohols What's meant by Reflux?
Continuously heating over a long period of time
38
# **Halogenoalkanes:** Forming Alcohols What is used in Reflux?
Warm Alkali (NaOH)
39
# **Halogenoalkanes:** Forming Alcohols What's a Reflux substitute?
Water (neutral nuclophile) ↳ reaction is slower
40
# **Halogenoalkanes:** Forming Alcohols Why's Water used as a substitute?
* Reaction is slower * OH- can be dissolved in water
41
# **Halogenoalkanes:** Forming Nitriles What do Halogenoalkanes react w to form Nitriles?
Potassium Cyanide (CN-) ↳provides Cyanide Ions which are triple bonded
42
# **Halogenoalkanes:** Forming Nitriles What's the Equation for this reaction?
43
# **Halogenoalkanes:** Forming Nitriles What's a Reflux Substitute for this reaction?
Ethanol ↳ Potassium Cyanide is insoluble in water but soluble in ethanol
44
# **Halogenoalkanes:** Forming Amines (NH2) What do Halogenoalkanes react w to form Amines?
**Excess** Ethanolic Ammonia ↳ ammonia dissolved in ethanol
45
# **Halogenoalkanes:** Forming Amines (NH2) Why's the Ethanolic Ammonia in **Excess**?
Ammonia reacts twice in this reaction
46
# **Halogenoalkanes:** Forming Amines (NH2) What's the Reaction mechanism for this?
47
# **Halogenoalkanes:** Forming Amines (NH2) What's the 1st Reaction w Ammonia?
Attacks the Halogen ↳ e- donated to C (δ+) which later passes it to X
48
# **Halogenoalkanes:** Forming Amines (NH2) What happens after the 1st Reaction w Ammonia?
* Dative bond is formed * N is +
49
# **Halogenoalkanes:** Forming Amines (NH2) Why does the 2nd Reaction w Ammonia occur?
You can't have a + on a compound
50
# **Halogenoalkanes:** Forming Amines (NH2) What happens in the 2nd Reaction w Ammonia?
Ammonia takes a proton from N+ ↳ removes a H from it creating an Amine
51
# **Halogenoalkanes:** Forming Amines (NH2) How would you Identify an Amine?
Smells fishy
52
# **Halogenoalkanes:** Elimination Reactions What is an Elimination Reaction?
When a Halogenoalkane reacts w Ethanolic Alkali instead of Aqueous
53
# **Halogenoalkanes:** Elimination Reactions What's the Equation for this reaction?
54
# **Halogenoalkanes:** Elimination Reactions Why's Reflux required for this Reaction?
Otherwise volatile stuff will be lost
55
# **Halogenoalkanes:** Elimination Reactions What occurs in this Reactions?
* Alkene formed * Reactants are dehydrated

Chemistry (13 decks)

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