Alcohols 3

Question 1
An organic compound J reacts with sodium to produce an organic ion with a charge of –3.
J reacts with NaOH (aq) to produce an organic ion with a charge of –1.
What could be the structural formula of J?
A. HO2CCH(OH)CH2CO2H
B. HO2CCH(OH)CH2CHO
C. HOCH2CH(OH)CH2CO2H
D. HOCH2COCH2CHO
Question 2
In a multi-step synthesis reaction, butanal is converted into a compound Z.
HCN, NaCN hot dilute H 2 SO 4 CH 3CH 2 OH, heat

CH 3 ( CH 2 ) CHO ⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯ X ⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯ Y ⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯ Z
2 trace of conc . H 2 SO 4
What could Z be?

A. CH3(CH2)3COOCH2CH3
B. CH3(CH2)2CH(OH)COOCH2CH3
C. CH3(CH2)CH(OH)COCH2CH3
D. CH3(CH2)2CH(OCH2CH3)COOH
Question 3
What will react differently with the two isomeric alcohols, (CH3)3CCH2OH and (CH3)2CHCH2CH2OH?
A. Sodium
B. Acidified aqueous potassium dichromate (VI)
C. Phosphorus pentachloride
D. Concentrated sulfuric acid
Question 4
Compound Q has the molecular formula C10H14O and is unreactive towards mild oxidising agents.
Which structure formed by the dehydration of compound Q?
A.
B.
C.
D.
Question 5
The foul smell that skunks spray is due to a number of thiols, one of which is methanethiol, CH3SH, which burns as follows.
CH3SH + 3O2 → CO2 + SO2 + 2H2O
A sample of 15 cm3 of methanethiol was exploded with 90 cm3 of oxygen.
What would be the final volume of the resultant mixture of gases when cooled to room temperature?
A. 30 cm3
B. 45 cm3
C. 75 cm3
D. 105 cm3
Question 6
1.50 g of butan-2-ol were mixed with excess acidified potassium dichromate (VI). The reaction mixture was then boiled
under reflux for fifteen minutes. The organic product was then collected by distillation. The yield of product was 80.0%.
What mass of product was collected?
A. 0.91 g
B. 1.17 g
C. 1.43 g
D. 1.46 g
1
The correct answer is C because:
 Sodium (Na) can react with both carboxylic acid –CO2H and alcohol –OH groups.
 Sodium hydroxide (NaOH) only reacts with the carboxylic acid –CO2H group.
 Consider option C:
o HOCH2CH(OH)CH2CO2H
 This compound contains 2 alcohol groups and 1 carboxylic acid group.

o In the reaction with sodium, Na would react with all 3 groups and hence form an organic ion
with charge –3.
o In the reaction with sodium hydroxide, NaOH would react with the carboxylic acid group
only and hence form an organic ion with charge –1.
 Therefore, option C is correct.
A is incorrect as this compound contains 2 carboxylic acid groups and 1 alcohol group. Na: reacts with all
3 groups and hence would form an organic ion with charge –3. NaOH: reacts with the 2 carboxylic acid
groups only and hence would form an organic ion with charge –2.
B is incorrect as this compound contains 1 carboxylic acid group, 1 alcohol group and an aldehyde
group. Na: reacts with the alcohol and carboxylic acid group and hence would form an organic ion with
charge –2. NaOH: reacts with the carboxylic acid group and hence would form an organic ion with
charge –1.
D is incorrect as this compound contains 1 alcohol group, 1 aldehyde group and 1 ketone group. Na:
reacts with the alcohol group only and hence would form an organic ion with charge –1. NaOH: reacts
with the no groups and hence would form an organic ion with charge 0.
2
The correct answer is B because:
 Butanal is an aldehyde which will undergo a nucleophilic addition reaction with HCN to form
a hydroxynitrile (compound X).
 Compound X is hydrolysed by reacting with hot dilute sulfuric acid to form a carboxylic
acid (compound Y) and ammonium sulfate salt.
 Compound Y reacts with the alcohol group of ethanol to form an ester (compound Z).
A is incorrect as the -OH group has been left out.
C is incorrect as the reaction of a carboxylic acid and alcohol gives an ester.
D is incorrect as ethanol reacts at the carboxylic acid group of compound Y, not at the alcohol group.
3
The correct answer is D because:
 When an alcohol reacts with concentrated sulfuric acid, dehydration takes place.
o Dehydration is the loss of a water molecule.
o This is an acid catalysed reaction because H2SO4 donates an H+ which is regenerated by
the production of H3O+ (which dissociates into H2O + H+).
 For dehydration to take place, the carbon atom adjacent to the alcohol must be bonded to
hydrogen atoms so can be deprotonated (lose a H+) to form a C=C bond – therefore,
(CH3)3CHCH2OH cannot be dehydrated.
A is incorrect as both alcohols contain an -OH group which will react with reactive metals such as Na to
form a salt and hydrogen gas.
B is incorrect as both alcohols contain a primary alcohol group which will get oxidised to a carboxylic
acid.
C is incorrect as both are primary alcohols which will undergo nucleophilic substitution of a chlorine atom
to form a primary halogenoalkane.
4
 Both ketones and tertiary alcohols are unreactive towards mild oxidising agents.
 However, alcohols undergo dehydration to form an alkene, therefore compound Q is a tertiary

alcohol.
A is incorrect as this is the dehydration product of a secondary alcohol which is reactive towards mild
oxidising reagents as they get oxidised to ketones.
B & D are incorrect as these are the dehydration product of primary alcohols which are reactive towards
mild oxidising reagents as they get oxidised to aldehydes and further oxidised to carboxylic acids.
5
 The question is about the total volume of gases when cooled to room temperature.
 At room temperature H2O is a liquid and not a gas so water can be disregarded.
 Volume of methanethiol combusted: 15 cm3.
 An initial, change and final volume table should be made as follows:
CH3SH O2 CO2 SO2

Initial (cm3) 15 90 0 0
Mole ratio 1 3 1 1
calculation 1 × –15 3 × –15 1 × +15 1 × +15
Change (cm3) –15 –45 +15 +15
calculation 15 – 15 90 – 45 0 + 15 0 + 15
Final volume (cm3) 0 45 15 15
 Since there is 45 cm3 of the initial 90 cm3 O2 left and 15 cm3 of CO2 and 15 cm3 of SO2 produced,
the total volume of gases is 75 cm3.
A is incorrect as the 45 cm3 of leftover O2 has not been added to the total volume of gases produced.
B is incorrect as this is the volume of O2 left.

D is incorrect as the volume of H2O has also been included in the total volume of gases however at room
temperature H2O is not a gas but a liquid.
6
The correct answer is B because:
 Butan-2-ol is a secondary alcohol and therefore will oxidise to the ketone butanone when
refluxed with acidified potassium dichromate (VI).
 Known quantities:
o Mass of butan-2-ol; 1.50 g
o Molecular weight of butan-2-ol; 74 g/mol from periodic table
o Percentage yield; 80.0%
o Molecular weight of product (butan-2-one); 72 g/mol from periodic table
 Calculate the moles of butan-2-ol:

o
 Calculate the yield of product in moles:

o moles x % yield = yield of product
o 0.0203 x 80 / 100 = 0.0162 mol of product
 Calculate the mass of butan-2-one formed:

o mass = moles × Mr = 0.0162 mol × 72 g/mol = 1.166 g = 1.17 g to 3 significant figures
A is incorrect as this would have been the mass of product if butan-2-ol was dehydrated to butene.
C is incorrect as this would have been the mass of product formed if butan-1-ol had been oxidised to
butanoic acid.
D is incorrect as this would have been the mass of the product if there was a 100% yield.

Alcohols 3

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Question 1

HCN, NaCN hot dilute H 2 SO 4 CH 3CH 2 OH, heat

What could Z be?

 This compound contains 2 alcohol groups and 1 carboxylic acid group.

 Therefore, option C is correct.

C is incorrect as the reaction of a carboxylic acid and alcohol gives an ester.

 However, alcohols undergo dehydration to form an alkene, therefore compound Q is a tertiary

 Volume of methanethiol combusted: 15 cm3.

 An initial, change and final volume table should be made as follows:

CH3SH O2 CO2 SO2

B is incorrect as this is the volume of O2 left.

 Calculate the moles of butan-2-ol:

 Calculate the yield of product in moles:

 Calculate the mass of butan-2-one formed:

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