Alcohol revision questions

1. This question is about organic compounds with the molecular formula C3H8O.

(a) Draw the structural formulae of the two isomers with molecular formula C3H8O
which are alcohols. Give the names of these alcohols.

Alcohol 1 Alcohol 2

Structural
formula

Name …………………………. …………………………

(4)

(b) Primary alcohols can be oxidised to carboxylic acids.

(i) Give the name and structural formula of the carboxylic acid formed when
the primary alcohol C3H8O is fully oxidised.

Name ................................................................................................................

Structural formula

(2)

(ii) State the reagents used for this oxidation.

Reagent
1 ..........................................................................................................

Reagent
2 ..........................................................................................................
(2)
(Total 8 marks)

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2. This question is about the alcohols labelled A – F and some of their reactions.
A B
CH 3 CH 3

C H 3C H C H C H 2C H 3 C H 3C H 2C H 2C C H 3

O H O H

C D
C H 2C H 2C H 2O H CH 3

C H 3C H 2C H 2 C H 3C H 2C C H 2O H

CH 3

E F
O H H O ––C H 2

C H 3C C H 2C H 3

CH 3

(a) (i) Two of the formulae A – F represent the same compound. Identify them by
letter and give the systematic name of this compound.

.........................................

.........................................

Systematic name ..............................................................................................

(2)

(ii) Select from A – F any tertiary alcohols. Explain how you would recognise a
tertiary alcohol from its structure.

..........................................................................................................................
.

..........................................................................................................................
.

..........................................................................................................................
.
(2)

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 (iii) Five of the alcohols A – F are isomers. Explain what is meant by isomers.

..........................................................................................................................
.

..........................................................................................................................
.

..........................................................................................................................
.
(2)

(b) (i) Give the letters of all the alcohols that would form carboxylic acids when
refluxed with acidified sodium dichromate(VI).

..........................................................................................................................
.
(1)

(ii) What type of reaction takes place during the formation of the carboxylic
acids?

..........................................................................................................................
.
(1)

(iii) What colour change would you expect to accompany the reaction?

From .................................................. to ..................................................

(1)

(c) (i) Alcohol E can be converted to a liquid alkene in a reaction with

concentrated phosphoric acid. Draw and label suitable apparatus to carry out
this reaction and collect the alkene formed.

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 (3)

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 (ii) 15.0 g of alcohol E formed 9.84 g of the alkene cyclohexene, after
purification.
Calculate the percentage yield of the reaction.

[Relative molecular mass, Mr, of alcohol E = 100, Mr of cyclohexene = 82]

(2)
(Total 14 marks)

3. Ethanol is a primary alcohol and can be oxidised if heated with an acidified solution of
potassium dichromate(VI). Two possible organic oxidation products may be obtained.

(i) Draw the full structural formula, showing all bonds, of both oxidation products.

(2)

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 (ii) Give the name and structural formula of an alcohol that would not be oxidised by
heating it with an acidified solution of potassium dichromate(VI).

(2)
(Total 4 marks)

4. Ethanol, C2H5OH, can be converted into ethanal, CH3CHO, if it is heated with an acid
and sodium dichromate(VI) solution, provided that the ethanal is immediately distilled
off.

A possible arrangement of apparatus for this experiment is shown below. However, it is

incompletely labelled and the diagram contains some errors. You may assume that the
apparatus is correctly clamped.

T h e rm o m e te r

W a te r in

Ite m B

Ite m A
E th a n o l + a c id
+ s o d iu m Item C
d ic h ro m a te (V I)
G auze W a te r o u t
To fu m e
H eat c u p b o a rd

Ic e c o ld
w a te r

E th a n a l

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 (a) What are the names of the three items labelled A, B and C?

A ................................................................................................................................
.

B ................................................................................................................................
.

C ................................................................................................................................
.
(3)

(b) List THREE errors in this diagram.

....................................................................................................................................
.

....................................................................................................................................
.

....................................................................................................................................
.

....................................................................................................................................
.

....................................................................................................................................
.

....................................................................................................................................
.

....................................................................................................................................
.

....................................................................................................................................
.

....................................................................................................................................
.
(3)

(c) Which acid should be used?

....................................................................................................................................
.
(1)

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 (d) What type of reaction is the conversion of ethanol to ethanal? Justify your answer
by considering their formulae.

....................................................................................................................................
.

....................................................................................................................................
.

....................................................................................................................................
.
(2)

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 (e) (i) What is the formula of the dichromate ion in sodium dichromate(VI)
Na2Cr2O7?

..........................................................................................................................
.
(1)

(ii) What colour change would you expect to see as the reaction proceeded?

Colour at start ...................................... Colour at

end ......................................
(1)

(f) If the mixture is refluxed first before being distilled, what is the name and formula
of the organic product?

Name .........................................................................................................................
..

Formula .....................................................................................................................
..
(2)
(Total 13 marks)

5. This question is about the reactions of a compound Z, CH3CH(OH)CH3.

(a) Name compound Z.

....................................................................................................................................
.
(1)

(b) Explain, in terms of its structure, why Z is classified as a secondary alcohol.

....................................................................................................................................
.

....................................................................................................................................
.
(1)

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 (c) Write an equation for the complete combustion of Z using the molecular formula
for Z. State symbols are not required.

(2)

(d) A small piece of freshly cut sodium was added to Z. Give TWO observations
which would be made.

....................................................................................................................................
.

....................................................................................................................................
.

....................................................................................................................................
.

....................................................................................................................................
.
(2)

(e) A few drops of Z were put in a boiling tube with a mixture of sodium
dichromate(VI) solution and dilute sulphuric acid and the mixture was warmed
gently until a reaction occurred.

(i) What colour change would be observed?

From
......................................................to .......................................................
...
(1)

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 (ii) Draw the displayed formula of the organic product of this reaction and
name it.

Name ......................................................................................................
...........
(2)

(iii) A pure sample of the organic product was mixed with Benedict’s solution.
State the colour of the mixture after it was warmed.

..........................................................................................................................
.
(1)

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 (f) A sample of Z was dehydrated using a solid dehydrating agent.

Draw a labelled diagram of the apparatus you would use to dehydrate Z and
collect the gaseous product.

(3)
(Total 13 marks)

6. Four of the structural isomers of C4H10O are alcohols. One of these isomers is butan-2-
ol.

(a) Draw the structural formulaE of two other alcohols with molecular formula C4 H10
O and name each of these isomers.

Diagrams

Isomer 1 Isomer 2

Name of isomer 1 Name of isomer 2

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 .......................................... ..........................................
(4)

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 (b) A sample of butan-2-ol, C4H9OH, was heated with a mixture of sulphuric acid and
potassium dichromate (VI).

(i) State the colour change that would be observed during the reaction.

..........................................................................................................................

..........................................................................................................................
(1)

(ii) Give the name of the organic product formed, and name the type of reaction
occurring.

..........................................................................................................................

..........................................................................................................................
(2)
(Total 7 marks)

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 Answers alcohols revision questions
1. (a) CH3CH2CH2OH (1)
Propan-1-ol (1)
CH3CH(OH)CH3 (1)
Propan-2-ol (1) 4

(b) (i) Propanoic acid (1)

CH3CH2CO2H (1) 2

(ii) Either
sodium dichromate ((VI))
or potassium manganate(VII) (1)

Sulfuric acid (1)

dependent on 1st mark
Ignore concentrated/dilute 2
[8]

2. (a) (i) D and F (1)

2,2-dimethylbutan(e)-1-ol (1)
conditional on the first mark

IGNORE punctuation 2
Reject but-1-ol and buta-1-ol

(ii) B / 2-methylpentan-2-ol (1)

carbon atom joined to hydroxyl group is attached to three

other carbon atoms (1)

mark independently 2
Accept carbon atom joined to hydroxyl group has no
hydrogens attached
Reject more than one given loses first mark

(iii) same molecular formula/same number and type of atoms (1)

different structural formula /different displayed formula/ different
arrangement of atoms (1) 2
Reject same chemical formula

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 Reject different structure (alone)

(b) (i) D, F and C (1) 1

Accept D and C
or
F and C

(ii) (complete)oxidation (1) 1

Accept redox
Reject reduction. partial

(iii) orange to green/blue (1) 1

(c) (i) round-bottomed or pear-shaped flask + heat (1)

condenser with correct water flow (1)
collection vessel (1)

Apparatus with no joints max 2 3

Accept 2 max for non working apparatus
Accept e.g. sealed

(ii) moles of cyclohexanol =15 /100 = 0.15

AND moles of cyclohexene = 9.84/82 = 0.12 (1)

0.12
% yield = 0.15 × 100 = 80%(1)

Correct answer alone (2) 2

Accept moles of cyclohexanol =15/100 = 0.15 and mass of
cyclohexene = 0.15 × 82 = 12.3 (1)
9.84
% yield = 12.3 × 100 = 80% (1)
[14]

3. (i)

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 H H O
H
H C C H C C
O O H
H H
(1 ) (1 ) 2
Accept –OH for –O — H

(ii) structural formula of any tertiary alcohol (1)

and its name (1) – must not contradict the formula and conditional
on tertiary alcohol 2
Accept 2nd mark can be awarded if minor slip in formula
or no formula given
[4]

4. (a) A round-bottom(ed)/distillation flask (1)

Accept Pear-shaped flask
Accept Flask
Accept long neck flask
Reject Liebig flask
Reject conical flask
Reject bottle ended flask
Reject volumetric flask

B (Liebig) condenser (1)

Accept condenser
Reject cooling water jacket
Reject condensing tube

C anti-bumping beads/granules (1) 3

Accept porcelain/ silica
Accept correct names in any order

(b) No stopper in top of flask (1)

Reject “side arm on conical flask not needed”

No jacket on condenser (1)

Water direction wrong way round (1)

Reject i.e. implying sealed apparatus

Ignore:/ neutral
“flask sealed off from rest of apparatus”
“water bath not needed”
“cork in conical flask not needed”
“gap between top of condenser & still head”

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 “air condenser sufficient”
“fume cupboard not needed”
Reject thermometer should be in liquid
Reject no need for anti bumping beads

If they give 4 or more errors : loses 1 mark for each “reject”

but neutral ones are ignored e.g.
3 correct + sealed apparatus = 3–1=2
3 correct+ water bath not needed = 3–0 = 3

[if this part is completely blank send to review under out of clip category] 3

(c) (concentrated) sulphuric/sulfuric acid 1

Accept dilute

(d) Oxidation (1) partial oxidation

hydrogen atoms lost (as organic reactant changes to product) (1) 2
Allow oxidation number of carbon increases (from –2 to –
1)
Accept redox if the rest of the answer makes clear that the
ethanol has been oxidised
Reject reduction
Reject redox

(e) (i) Cr2O72– 1

(ii) Orange to green 1

Accept blue

(f) Ethanoic acid (1)

CH3CO2H / CH3COOH (1)
Mark independently 2
Accept correct structural or displayed formula
Accept molecular formula C2H4O2 correct if name is
correct
Reject empirical formula
Reject C2H3OOH, CH3CHO2
[13]

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5. (a) Propan-2-ol
NOT prop-2-ol/ 2-propanol 1

(b) Contains C H O H or fully displayed

OR carbon carrying OH/ hydroxyl/ “hydroxide” group attached to two

other carbons/ two other methyl groups/ one other hydrogen
ALLOW contains CHOH/CH (OH)
NOT references to hydroxide ion/ OH– in explanation 1

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 9
(c) C3H8O + 2 O2 → 3CO2 + 4H2O

OR

2C3H8O + 9O2 → 6CO2 + 8H2O

products (1)
balancing of equation based on correct products (1)
9
ALLOW 4.5, 4½ for 2
IGNORE state symbols
No penalty if structural formulae used 2

Bubbles/effervescence/ fizzing (1) 

Gets hotter/ heat produced/temperature rises (1) 

NOT exothermic 

Sodium dissolves/disappears/ gets smaller(1) 
White solid produced(1) 

(d) Hissing sound (1)  any two

NOT white precipitate

NOT floats/moves around and goes on fire 2

(e) (i) Orange to green/blue 1

(ii)
H H
H C C C H
H O H (1)
MUST be fully displayed

Propanone/ propan(e)-2-one (1)

ALLOW acetone
No TE from incorrect formula 2

(iii) Blue / light blue

NOT mention of any other modified colour of blue
ie NOT blue-green 1

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 (f)

c e ra m ic fib re Z
s o a k e d in

B unsen
v a lv e
heat
a lu m in iu m o x id e
g ra n u le s
or w a te r
a lte rn a tiv e
s o lid
d e h y d ra tin g
agent

c e ra m ic fib re
s o a k e d in

B unsen
v a lv e
heat
a lu m in iu m o x id e
g ra n u le s
or w a te r
a lte rn a tiv e
s o lid
d e h y d ra tin g
agent
3

Tube + contents (1)

ALLOW glass wool/ mineral wool/ Rocksil wool
NOT wire wool/ cotton wool

Heat under some solid (1)

Gas collected by displacement of water – water does not

need to be labelled
OR collect in syringe (1)
IGNORE open tube following Bunsen valve, providing gas
can be collected

–1 for each error

eg single line tube; gap between bung and tube; delivery tube
through side of trough, delivery tube not under collecting tube
[13]

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6. (a) Diagrams:
H H
H C H H C H
H H H H H H H H
H C C C C O H H C C C H H C C C O H
H H H H H O H H H H H
Any two (2)

Names:
Butan-1-ol, (2)-methylpropan-1-ol,
(2)-methylpropan-2-ol any two (2) 4

(b) (i) From orange to (blue-)green (1) 1

(ii) butan-(2)-one (1)

Oxidation/redox (1) 2
[7]

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