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ORGANIC WS 10 8- AMINO ACIDS

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The amino acids tyrosine, lysine and glycine are constituents of many proteins.
The amino acids tyrosine, lysine and glycine are constituents of many proteins.
O
O

H 2N
H2N

CH
CH

C
C

CH
CH22

OH
OH

O
O
H N
H22N

CH
CH

C
C

(CH2)4
(CH2)4
NH2
NH2

OH
OH

lysine
lysine

tyrosine
tyrosine

O
O

OH
OH
H2N
H2N

CH
CH

C
C

OH
OH

H
H

glycine
glycine

(a) State the reagents and conditions you could use to break proteins down into amino
(a) State
acids.the reagents and conditions you could use to break proteins down into amino
acids.
..................................................................................................................................... [2]
..................................................................................................................................... [2]
(b) Draw a ring around each chiral centre in the above molecules.
[1]
(b) Draw a ring around each chiral centre in the above molecules.
[1]
(c) In aqueous solution amino acids exist as zwitterions. Draw the zwitterionic structure of
(c) Inglycine.
aqueous solution amino acids exist as zwitterions. Draw the zwitterionic structure of
glycine.

..................................................................................................................................... [1]
..................................................................................................................................... [1]
(d) For each of the following reactions, draw the structure of the organic compound formed.

(d) For each of the following reactions, draw the structure of the organic compound formed.
(i) glycine + excess NaOH(aq)
(i)

glycine + excess NaOH(aq)


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

(ii)

(ii)

...................................................................................................................................
tyrosine + excess NaOH(aq)
tyrosine + excess NaOH(aq)
...................................................................................................................................

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

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(iii)

lysine + excess HCl (aq)


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

(iv)

tyrosine + excess Br2(aq)


...................................................................................................................................
[5]

(e) Draw the structural formula of a tripeptide formed from all three of these amino acids,
showing clearly the peptide bonds.

..................................................................................................................................... [2]
(f)

CH2 NH

The formula of part of the chain of a synthetic polyamide is shown below.

CO

(i)

CO NH CH2 CH2 NH

CO

CO NH CH2 CH2 NH

Identify the repeat unit of the polymer by drawing square brackets around it on the
above formula.

(ii) Draw the structures of the two monomers from which the polymer could be made.

...................................................................................................................................
[3]
[Total: 14]

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27

(a) Explain briefly what is meant by the word protein.


..........................................................................................................................................
.................................................................................................................................... [1]
(b) Describe how peptide bonds are formed between amino acids during the formation of a
tripeptide. Include diagrams and displayed formulae in your answer.

.................................................................................................................................... [3]
(c) Describe how proteins can be broken down into amino acids in the laboratory without
the aid of enzymes.
.................................................................................................................................... [2]
(d) When a small polypeptide S was broken down in this way, three different amino acids
were produced according to the following reaction.

3 NH2CH2CO2H

2 NH2CHCO2H

CH3

Mr = 75

2 NH2CHCO2H
CH2

Mr = 89
Mr = 165

(i)

How many peptide bonds were broken during this reaction?


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

(ii)

Calculate the Mr of the polypeptide S.

Mr = .....................................................
[3]
[Total: 9]

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Much research has been carried out in recent years investigating the exact structure of silk.
The silk of a spiders web is at least five times as strong as steel, and twice as elastic as
nylon. A silk fibre is composed of many identical protein chains, which are mainly made from
the amino acids glycine, alanine and serine, with smaller amounts of four other amino acids.
NH2CH2CO2H

NH2CHCO2H
|

NH2CHCO2H

CH3
glycine

alanine

CH2OH
serine

(a) Amino acids can exist as zwitterions. Draw the zwitterionic structure for glycine.

[1]
(b) Amino acids can act as acids or bases. Write equations to show:
(i)

the reaction between alanine and HCl(aq),


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

(ii)

the reaction between serine and NaOH(aq).


...................................................................................................................................
[2]

(c) Draw the structural formula of a portion of the silk protein, showing three amino acid
residues. Label a peptide bond on your structure.

[3]
(d) What type of polymer is silk protein?
......................................................................................................................................[1]

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(e) The Mr of a silk protein molecule is about 600,000. Assuming it is made from equal
amounts of the above three amino acids, calculate the average number of amino acid
residues in the protein chain. [Mr (glycine) = 75; Mr (alanine) = 89; Mr (serine) = 105]

number of residues = ................................... [3]


[Total: 10]

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45

The amino acid alanine, K, can be obtained from 2-hydroxypropanoic acid, H, by the
following route.
CH3CH(OH)CO2H
H

I
CH3CHClCO2H
J

II
CH3CH(NH2)CO2H
K

(a) Suggest a test you could use to distinguish H from its isomer 3-hydroxypropanoic acid, L.
HOCH2CH2CO2H
L
reagents ...........................................................................................................................
observation with H ............................................................................................................
observation with L ........................................................................................................[2]
(b) How would the acidity of chloropropanoic acid, J, compare with that of propanoic acid?
Briefly explain your answer.
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[2]
(c) Alanine reacts with both acids and bases.
Write an equation for the reaction between alanine and sodium hydroxide, drawing the
displayed formula of the organic product.

[2]
(d) In solution, alanine exists as a zwitterion. Draw the structure of this ion.

[1]

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(e) Alanine is one of about 20 amino acids that make up proteins.
(i)

What type of bond joins amino acids together in proteins?


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

(ii)

Draw the displayed formula of the compound formed when two alanine molecules
are joined by this bond.

[2]
(f)

An excess of benzoic acid in the body (present as a preservative in many foodstuffs, or


formed by oxidation of aromatic compounds present in food) is excreted as hippuric
acid, M.

CONHCH2CO2H
M
(i)

Suggest a reagent that could be reacted with glycine in the laboratory to form
hippuric acid.
...................................................................................................................................

(ii)

Suggest the reagents and conditions needed to re-form glycine from hippuric acid.
...................................................................................................................................
...................................................................................................................................
[3]
[Total : 12]

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(c) A good way of making synthetic amino acids uses chloro-acids as intermediates.

CH3CH2CO2H

(i)

Cl2 + trace of P
I

CH3CHCl CO2H

NH3(excess)
II

CH3CH(NH2)CO2H
alanine

Suggest the role that the trace of phosphorus plays in reaction I.


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

(ii)

Write a fully balanced equation for reaction I.


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

(iii)

State the type of mechanism of reaction II.


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

(iv)

When 10.0 g of propanoic acid was used in this 2-stage synthesis, a yield of 9.5 g of
alanine was obtained.
Calculate the overall percentage yield.

..................................................................................................................................
[5]
(d) In the solid state and in aqueous solutions, alanine exists as a zwitterion.
Draw the structural formula of this zwitterion.

[2]
[Total: 15]

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