TOPIC-15 SET-3

Q1. One industrial use of methanol is in the production of bio-diesel from vegetable oils.
A component of these oils is shown below.

Complete the equation for the reaction of methanol with this compound.
(2)

Q2. This question is about the isomers P and Q.

(a) Identify the reagent used in a test to show that P and Q are both carbonyl compounds.
Give the positive result of the test.
(2)
Reagent
.............................................................................................................................................
Result
.............................................................................................................................................
(b) Identify the reagents used in a test which gives a positive result with P but not with Q.
Give the positive result of the test and identify the organic product which is observed.
(3)
Reagents
.............................................................................................................................................
Result
.............................................................................................................................................
Identity of organic product
.............................................................................................................................................

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(c) Name the organic product formed when P reacts under suitable conditions with lithium
tetrahydridoaluminate(III).
(1)
.............................................................................................................................................
(d) The proton nmr spectra of P and Q were compared. Complete the table.
(4)

(e) A sequence of reactions was carried out with Q.

(i) Complete the mechanism for the reaction of Q with HCN in the presence of NaCN,
showing relevant curly arrows, lone pairs, charges and dipoles.
(4)

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 (ii) Identify the reagent A used to convert compound R to compound S.
(1)
.............................................................................................................................................
(iii) Draw the displayed formula of two repeat units of polymer T.
(2)

Q3. When ethane-1,2-diol, HOCH2CH2OH, forms a polymer with benzene 1,4-dicarboxylic acid,
HOOCC6H4COOH, the repeat unit of the resulting polymer is

A −OCH2CH2OOCC6H4CO−
B −OCH2CH2OCC6H4CO−
C −OC6H4OOCCH2CH2CO−
D −CH2CH2OOCOC6H4OCO−

Q4. A polymer has the repeat unit.

It could be made from the monomers

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Q5.The molecule shown below was reacted with excess lithium tetrahydridoaluminate(III)
(lithium aluminium hydride) in dry ether, followed by the addition of acid.

The product of the reaction is

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Q6. The organic product of the reaction between ethanoyl chloride and methylamine has the
formula

Q7. A solution of 2,4-dinitrophenylhydrazine (Brady's reagent) is used as a test for organic

functional groups.

(a) The positive result of the test is the formation of

(1)

A a yellow solution.
B an orange precipitate.
C a red solution.
D a green precipitate.

(b) Which of the following gives a positive result with a solution of 2,4-dinitrophenylhydrazine?
(1)

A Only aldehydes
B Only ketones
C Only aldehydes and ketones
D Any compound containing the C O group

(c) The initial attack by 2,4-dinitrophenylhydrazine, when it reacts, is by

(1)

A a free radical.
B an electrophile.
C a nucleophile.
D a negative ion.

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(d) The product of a positive test, a 2,4-dinitrophenylhydrazone, contains which of the following
bonds?
(1)

A N N
B C N
C C C
D C O

Q8. Ketones react with

A both 2,4-dinitrophenylhydrazine solution and Tollens' reagent.

B 2,4-dinitrophenylhydrazine solution but not with Tollens' reagent.
C Tollens' reagent but not with 2,4-dinitrophenylhydrazine solution.
D neither Tollens' reagent nor 2,4-dinitrophenylhydrazine solution.

Q9. Ethanoic acid, CH3COOH, may be prepared from ethanenitrile, CH3CN. This reaction is
best described as

A reduction.
B oxidation.
C hydrolysis.
D condensation.

Q10. A flow chart for making 2-hydroxy-2-methylpropanoic acid from propan-2-ol is shown
below.

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(a) (i) Give the reagents and conditions for Step 1.
(2)
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................

(ii) Propanone is formed in Step 1.

Give a chemical test to identify the carbonyl group and a further test to show the presence

of the group.
For both tests, give the observations that you would make.
(4)
Carbonyl group
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................

group
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................

(b) (i) In Step 2, propanone undergoes an addition reaction with HCN in the presence of CN−
ions.
Give the mechanism for this reaction.
(3)

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 (ii) Explain why this reaction would not take place at either a very low or very high pH.
(2)
Low pH
.............................................................................................................................................
.............................................................................................................................................
High pH
.............................................................................................................................................
.............................................................................................................................................

(c) (i) The reaction in Step 3 forms 2-hydroxy-2-methylpropanoic acid, (CH3)2C(OH)COOH.

Suggest the type of reaction occurring in Step 3.
(1)
.............................................................................................................................................

(ii) Explain why the presence of the alcoholic hydroxyl group cannot be confirmed in the
infrared spectrum of 2-hydroxy-2-methylpropanoic acid.
(1)
.............................................................................................................................................
.............................................................................................................................................

(iii) The hydrogen of the alcohol group in 2-hydroxy-2-methylpropanoic acid can be identified
by a single peak in the nmr spectrum.
Give the chemical shift you would expect for this peak.
(1)
.............................................................................................................................................

(iv) How many peaks would you expect in a high resolution nmr spectrum for 2-hydroxy-2-
methylpropanoic acid, (CH3)2C(OH)COOH?
(1)
.............................................................................................................................................

(v) Explain why, in high resolution nmr, the peak due to the hydrogens of the 2-methyl group
in 2-hydroxy-2-methylpropanoic acid is a singlet.
(1)
.............................................................................................................................................
.............................................................................................................................................

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 (vi) Would you expect 2-hydroxy-2-methylpropanoic acid to have optical isomers?
Justify your answer.
(1)
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................

(d) (i) Molecules of 2-hydroxy-2-methylpropanoic acid react together to form a condensation

polymer.
Draw a displayed formula for this polymer, showing two repeating units.
(2)

(ii) Give the name of the functional group that links the two molecules in the polymer.
(1)
.............................................................................................................................................

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