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4.8.4d: HW Organic chemistry and spectroscopy (52 Marks)

1. Molecule P has the molecular formula C3H6O3.
(a) What can be deduced by the structure of P from the following information?
(i) P reacts with sodium hydrogencarbonate solution to produce effervescence.
(ii) P reacts with acidified potassium dichromate(VI) to form a green solution and
product R with the molecular formula C3H4O3.
(iii) P and R each react with sodium hydroxide and iodine to form a yellow precipitate.
(iv) P does not react with 2,4-dinitrophenylhydrazine but R does.
(v) P reacts with lithium tetrahydridoaluminate to form a compound with the formula
C3H8O2.

[7]

(b) The proton nmr of P reveals the following data:

Chemical shift /ppm
11.9
4.0
3.4
1.2

Split of the peak

singlet
quadruplet
singlet
doublet

Use the data and the inferences you made in part (a) to identify the structure of P.
Include a description of the proton environments responsible for the chemical shifts
and explain the splitting pattern of the peaks.

[6]
(c) P can form a polymer. Draw two repeats of the polymer and name the linkage present
in the polymer.

[2]
[Total: 15]
2

2. The following reaction scheme shows some of the reactions that

(a) State the reagents and conditions for the steps shown in the reaction scheme above.
Reaction step

Reagents/reactants

Conditions

1
2
3
4
5
6
7
[14]
3

(b) Draw the structure of H.

[1]
(c) Draw the organic products J and K.
J

[2]
(d) Name compound C.

[1]
(e) The product formed in step 2 has no optical activity. Explain why not?

[3]
(f) Draw the curly arrow mechanism for the reaction in step 2. Include relevant dipoles.

[4]
[Total: 25]
4

An unknown aldehyde T, C5H10O, was analysed using different techniques.

(a) (i)

Describe a chemical test that could be used to confirm that compound T is an aldehyde.
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.......................................................................................................................................[2]

(ii)

Identify the functional group formed in this chemical test.

.......................................................................................................................................[1]

(b) Describe a chemical method that could be used to confirm the presence of the carbonyl
group in compound T.
Explain how you would use the product of this test to identify compound T.
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...............................................................................................................................................[3]
(c) In a mass spectrum of compound T, determine the m/e value of the molecular ion peak.
...............................................................................................................................................[1]
(d) There are the four possible structural isomers for the aldehyde T, C5H10O. Two structures are
shown below.

isomer 1

O
C

H
H

CH3

O
C
H

isomer 2

(i)

Draw the skeletal formula for structural isomer 2.

[1]
(ii)

Draw the two other possible structural isomers of the aldehyde T, C5H10O.

[2]

absorption of energy

(e) The proton n.m.r. spectrum of aldehyde T is shown below.

12

11

10

7
6
5
chemical shift /ppm

Identify aldehyde T. Explain your reasoning.

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...............................................................................................................................................[2]
[Total: 12]