Ozone: Nucleophilic Substitution

Question 1

Give three examples of nucleophiles

Answer 1

1. :OH
2. H2O:
3. :NH3

Question 2

Definition of a nucleophile

Answer 2

An electron rich species with at least one lone pair of electrons attracted to regions of electron deficiency ( ie +ve charge ) and forms a covalent bond with a delta +ve C

Question 3

Definition of substitution

Answer 3

A reaction in which one atom or group in a molecule is replaced by another atom or group

Question 4

Be able to draw the nucleophilic substitution mechanism for 1-bromopropane + dilute aqueous NaOH

Nucleophile = :OH

Answer 4

Look at sheet

Question 5

Be able to draw the nucleophilic substitution mechanism for 1-bromopropane + water ( warm/steam)

Nucleophile = H2O:

Answer 5

Look at sheet

Question 6

Be able to draw the nucleophilic substitution mechanism for 1-bromopropane + ammonia ( heat in a sealed tube )

Nucleophile = :NH3 ( x2)

Answer 6

Look at sheet

Question 7

Given:

C-Cl
C-Br
C-I

Describe their polarity

Answer 7

• Polarity decreases as you go down the group
• C-Cl = most polar
• C-I = least polar

Question 8

Given:

C-Cl
C-Br
C-I

Describe their bond enthalpy

Answer 8

• Bond enthalpy decreases as you go down the group
• C-Cl = highest
• C-I = lowest

Question 9

How do you determine reactivity and why

Answer 9

• By bond enthalpy not polarity
• Because bond enthalpy takes precedent over polarity

Therefore C-I breaks first because lowest bond enthalpy = most reactive