15. Haloalkanes Flashcards

1
Q

Define a nucleophile.

A

an electron pair donor

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2
Q

What do all nucleophiles possess?

A

at least one lone pair

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3
Q

What are the 4 common nucleophiles?

A

OH- , CN- , NH3, H2O

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4
Q

Define hydrolysis.

A

the breaking of a chemical compound into 2 products, using H2O or OH-

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5
Q

What governs the rate of hydrolysis? Therefore do weaker or stronger bonds hydrolyse faster?

A

bond strength

weaker bonds: e.g. C-I

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6
Q

Why is C-I the weakest C-halogen bond?

A

I = larger atom = more shielding = less nuclear attraction to bonding pair = weaker bond

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7
Q

Does the rate of hydrolysis increase or decrease from C-I to C-F ?

A

decreases up the group

C-I hydrolyses faster than C-F

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8
Q

Which is the most polar C-halogen? What does this mean for it?

A

C-F
greatest difference in electronegativity
it attracts nucleophiles better an has the highest bond enthalpy

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9
Q

Describe an experiment to measure RoH.

A
  1. add equal vol. 1-iodopropane, 1-bromopropane and 1-chloropropane to equal vol. of ethanol in separate test tubes
  2. warm mixture to 50 degrees in a water bath and add equal vol. of AgNO3
  3. record time taken for precipitate to form
    • -white (Cl) appears last, yellow (I) appears first
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10
Q

Why do you add ethanol to the haloalkane when measuring RoH?

A

ethanol = v good solvent

has H bonding so dissolves aqueous/ionic and LDFs so dissolves organic

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11
Q

What does ozone do for us?

A

prevents genetic damage and cancer by absorbing UVB rays from the sun

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12
Q

What is the steady state of ozone? (reversible reaction)

A

O2 + O. <> O3

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13
Q

What happens to CFCs when they reach the ozone layer?

A

UV rays break C-Cl bond, as it has the lowest enthalpy, into Cl. radicals.

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14
Q

Write out the set of equations for ozone depletion by chlorine radicals.

A

go find it somewhere in ur little book

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15
Q

What is the overall equation for ozone depletion?

A

O3 + O => 2O2

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16
Q

What other radical catalyses ozone depletion? How is it formed?

A

NO.

formed in lightning strikes and by air travel

17
Q

Write out the set of equations for ozone depletion by NO. radicals.

A

go find it somewhere in ur little book

18
Q

What kind of mechanism do haloalkanes undergo?

A

nucleophilic substitution

19
Q

Draw out the nucleophilic substitution of chloroethane and NaOH

A

go find ur book katherine

20
Q

What are the conditions for the nucleophilic substitution of a haloalkane?

A

sodium or potassium hydroxide solution and reflux

21
Q

Why does the AgNO3 have to be aqueous when precipitating with haloalkanes?

A

the H2O in the solution acts as a nucleophile to cleave the halogen from the haloalkane
creates a halide ion that can bond to the Ag+ ions to form the precipitate

22
Q

Which stage of branching of haloalkanes hydrolyse the fastest? Why?

A

tertiary haloalkanes

more stable

23
Q

What are nucleophiles attracted to in a haloalkane?

A

the slightly +ve (e- deficient) Carbon

24
Q

What is the initiation step for the ozone depletion with CFCs?

A

CF2Cl2 => CF2Cl. + Cl.

25
Q

What do radicals act as in ozone depletion?

A

catalysts