Organic synthesis Mark scheme

Question 1

Give the IUPAC name for CH2(OH)CH(CH3)CH2Br

Answer 1

3-bromo-(2)-methylpropan-1-ol ONLY

Question 2

Reaction 1 occurs via a nucleophilic substitution mechanism.

Explain why the halogenoalkane is attacked by the nucleophile in this reaction.

Answer 2

Bromine is more electronegative than carbon

C is partially positive / electron deficient

M2 and M3 can be awarded from diagram that shows nucleophilic attack

Lone/electron pair (on the nucleophile) donated to the partially positive carbon

Question 3

Give the reagent and conditions for Step 1.

State how you could obtain a sample of the alcohol from the reaction mixture formed in Step 1.
step 1 is the conversion of an ester to a sodium salt and an alcohol

Answer 3

M1 NaOH
M2 aqueous ( warm )
M3 fractional distillation

Question 4

why would ammonia be unexpected for a reaction with benzene

Answer 4

Ammonia is a nucleophile

benzene repels nucleophiles

Question 5

Concentrated sulfuric acid reacts with solid sodium chloride.
Give the observation you would make in this reaction.
State the role of the sulfuric acid.
Observation with sodium chloride ________________________________________
___________________________________________________________________
Role of sulfuric acid

Answer 5

white / misty / steamy fumes

acid/proton donor

Question 6

Concentrated sulfuric acid reacts with solid sodium iodide, to produce several products.
Observations made during this reaction include the formation of a black solid, a yellow solid and a gas with the smell of bad eggs.
Identify the product responsible for each observation.
Black solid _________________________________________________________
Yellow solid _________________________________________________________
Gas

Answer 6

iodine / I2
IGNORE state symbols

sulfur / S / S8
If name and formula given they must both be right

hydrogen sulfide / H2S