page 20

Question 1

Problem 1: Identify the Nucleophile, Leaving Group, and Draw the Products

Answer 1

Reaction a:
Substrate:
CH3CH2CH2Br(1-bromopropane).
Nucleophile:
OCH2CH3−(ethoxide ion).
Leaving Group:
Br−(bromide ion).
Product:
CH3CH2CH2OCH2CH3
(1-propoxyethane).

Reaction b:
Substrate: Cyclohexyl chloride (
Cl on cyclohexane).
Nucleophile:
OH−(hydroxide ion).
Leaving Group:
Cl−(chloride ion).
Product: Cyclohexanol (
OHon cyclohexane).

Reaction c:
Substrate:
CH3CH2I (ethyl iodide).
Nucleophile:
N3− (azide ion).
Leaving Group:
I−(iodide ion).
Product:
CH3CH2N3
(ethyl azide).

Reaction d:
Substrate: Cyclohexyl bromide (Br on cyclohexane).
Nucleophile:
CN−(cyanide ion).
Leaving Group:
Br−(bromide ion).
Product: Cyclohexyl cyanide (CN on cyclohexane).

Question 2

Draw Products for Neutral Nucleophiles

Answer 2

Reaction a:
Substrate:
CH3CH2CH2Br(1-bromopropane).
Nucleophile:
N(CH2CH3)3
(triethylamine).
Intermediate Product:
CH3CH2CH2N+(CH2CH3)3
(quaternary ammonium salt).
Final Product: No proton loss occurs as
N(CH2CH3)3 forms a stable salt.

Reaction b:
Substrate:
(CH3)3C−Cl(tert-butyl chloride).
Nucleophile:
H2O (water).
Intermediate Product:
(CH3)3C−OH2+
Final Product:
(CH3)3C−OH (tert-butanol) after proton loss.