[Maximum number: 3]

Indigo is the dye used in blue jeans. Although originally extracted from plants of the type indigofera, it is now almost entirely made artificially.

Indigo is insoluble in water but this disadvantage can be overcome by converting it into the water-soluble colourless leuco-indigo. If cloth soaked in a solution of leuco-indigo is left to dry in the air, the leuco-indigo is converted into the insoluble blue indigo, which is precipitated out onto the fibres of the cloth.

(a)

(i)

Name three functional groups in indigo.

[ 3 ]

[Maximum number: 10]

The compound trans-4-hydroxy-2-nonenal (HNE) is thought to lead to infections of the lung when cigarettes are smoked.

\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CH}(\mathrm{OH}) \mathrm{CH}=\mathrm{CHCHO}

trans-4-hydroxy-2-nonenal

(a)

(i)

HNE contains an alkene group. Name as fully as you can two other functional groups which are present in the HNE molecule.

[Maximum number: 1]

The structure of compound Y is shown.

(a)

Samples of organic compounds, A, B, C and D, are placed in unlabelled bottles.
A
$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{3}$
B
$\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{CHO}$
C
$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$
D
$\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$

[ 1 ]

(i)

Identify all of the compound(s), A-D, that contain a carbonyl group.

[ 1 ]

(a)

1,3-dichloropropan-2-ol can be made by reacting M.

[ 1 ]

(i)

Name the functional group present in M that changes during this reaction.

[ 1 ]

(a)

Under suitable conditions, compound E will react with compound B.

[ 3 ]

(i)

What functional group is produced in this reaction?

[Maximum number: 2]

Although there are many different types of food eaten around the world, animal fats and/or vegetable oils are commonly used in cooking.

Animal fats and vegetable oils are usually glyceryl esters, that is esters of glycerol, propane-1,2,3-triol.

Many animal fats contain esters of stearic acid, $\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{16} \mathrm{CO}_{2} \mathrm{H}$ .
Vegetable oils often contain esters of oleic acid, $\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{7} \mathrm{CH}=\mathrm{CH}\left(\mathrm{CH}_{2}\right)_{7} \mathrm{CO}_{2} \mathrm{H}$ .

(a)

(i)

The ascorbic acid molecule contains three functional groups.

Two of these are alcohol (primary and secondary) and alkene.
What is the name of the third functional group?

[ 2 ]

[Maximum number: 14]

Astronomers using modern telescopes of various types have found many molecules in the dust clouds in space. Many of these molecules are those of organic compounds and astronomers constantly look for evidence that amino acids such as aminoethanoic acid, $\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CO}_{2} \mathrm{H}$ , are present.

One molecule that has been found in the dust clouds is hydroxyethanal, $\mathrm{HOCH}_{2} \mathrm{CHO}$ .

(a)

Hydroxyethanal contains two functional groups.

[ 7 ]

(i)

Name, as fully as you can, each of the functional groups present in hydroxyethanal.

1
2

[Maximum number: 1]

Compound V is a liquid.
V contains 77.2 % carbon, 11.4 % hydrogen and 11.4 % oxygen by mass.
V has a relative molecular mass of 280 .

(a)

W, X and Y have the same molecular formula, $\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}$ .

W, X and Y are added separately to different reagents. Observations for these reactions are described in Table 4.1.

Table 4.1

[ 1 ]

(i)

W, X and Y each contain a common functional group.

Name the functional group that is present in all three compounds.

[ 1 ]

[Maximum number: 3]

Noradrenaline is a hormone and neurotransmitter, which is released during stress to stimulate the heart and increase blood pressure.

noradrenaline

(a)

State the names of three functional groups in the noradrenaline molecule.

[ 3 ]

(a)

Compound G can be synthesised from benzene by the route shown below.

[ 1 ]

(i)

Name the functional group formed in step 5.

[ 1 ]

(b)

In a reaction discovered just over 100 years ago by the German chemist Karl Fries, compound G is converted into compound K when it is heated with $\mathrm{AlCl}_{3}$ . Compound K is a structural isomer of G.

Compound K is a 1,4 -disubstituted benzene derivative. It is insoluble in water, but dissolves in NaOH(aq). It gives a white precipitate with $\mathrm{Br}_{2}(\mathrm{aq})$ , and a yellow precipitate with alkaline aqueous iodine.

[ 2 ]

(i)

Use the information given above to name two functional groups in compound K.

[ 2 ]