F324 Amino Acids, Polymers & Synthesis HW (MS)
1.	(a)	(i)	is an amine and a carboxylic acid /
contains both NH2 and COOH functional groups (1) AW	1
(ii)	RCH(NH2)COOH (1)
	Does not fit the formula because NH2 and COOH are not
attached to the same carbon (1) AW	2
 (b)	(i)
	1
(ii)	–COO– becomes –COOH (1)
(rest of structure unaffected)
(allow ecf on rest of the structure)	1
 (c)

displayed peptide bond (1)
rest of the structure also correct (1)
(allow full marks for a correct anhydride structure)	2
[7]
 
2.	(i)	one amide link shown correctly (1)
glycine and phenylalanine parts shown correctly (1)
proline linked correctly (1)	3
(ii)	6 (1)	1
(iii)	gas/liquid chromatograph separates the tripeptides (1)
mass spectrometer produces a distinctive fragmentation pattern (1)
identification by computer using a spectral database (1)	3
[7]

3.	(i)	water / evidence of a solution in water – eg
(aq), ‘dil’ ,’6M’ or ‘ conc’ for HCl (1)
NOT conc HNO3
or conc H2SO4
	a named strong acid or alkali (heated under) reflux /
a suitable enzyme at around 37°C (1)	2
(ii)	amino acids (1)	1
(iii)	correct structure for one of the amino acids (1)
correct ionic form for reagent used in a(i) – eg

	/	(1)	2
(iv)	reaction with water to split/break down the compound (1)
	peptide bond in the compound is broken / diagram to show AW (1)	2
[7]

4.	General formula of an α-amino acid
	 (1)
	Diagram to show length of polypeptide / repeat unit – eg

	with:
	displayed peptide bond (1)
	correct structure with a minimum of two amino acids joined
(can be scored by a dipeptide) (1)
	idea of polymerisation shown by ‘end bonds’ (1)
	loss of water (1)
	relate variety to different R groups / sequence of amino acids
(1) AW	6
	Quality of written communication:
correct organisation and use of both of the terms:
condensation polymer(isation) and peptide bond/link (1)	1
[7]

5.	(i)
 
ALLOW RCH(NH2)COOH any order for R, NH2 and COOH but C must be next to H ‘CH’ must be shown
ALLOW CO2H
brackets around NH2 are not essential
ALLOW structure
1
(ii)	must attempt 3D
	use  symbol in the “tools” to denote whether or not each chiral C
is a reflection of the one given in the question

each chiral C must have 2 — bonds, 1 wedge bond (IGNORE shading) & 1 dash bond (IGNORE wedge)
check the clockwise orientation of each C. For each C start with the H and if on the:
•	top C the H is followed by COOH it is not a mirror image.
	If it is a mirror image annotate using RE.
•	bottom C the H is followed by CH3 it is not a mirror
	image. If it is a mirror image annotate using RE.
the four groups can be attached in any order. If the molecule is drawn upside down – clockwise becomes anti-clockwise.
MUST check that the drawn structure is non-superimposable irrespective of the orientation or the way it has been drawn.
IGNORE bond linkage for all groups
3
[4]

 6.	(a)	(i)	H2NCHRCOOH /  (1)	1
allow R CH NH2 and COOH in any order
(ii)	they both have the  group / or in words (1)
NOT just “they both have NH2 and COOH”
	R group is H in glycine and CH2CH2COOH in glutamic acid (1)	2

(b)
	–NH3+ (1)
-COOH and side chain unaffected (1)		one –COO– (1)
both –COO– (1)
H2N- and rest of molecule (1)	
		5
(c)	glutamic acid/molecule with optical isomers …
	… is chiral (1)
	… has four different / distinguishable groups attached to a carbon (1)
NOT just “different atoms”
	… the mirror images/isomers cannot be superimposed AW (1)
	one diagram showing two 3-D bonds not opposite each other,
and not with angles looking like 90°  (1)
	3-D diagram of the other isomer (allow ecf on one 3-D error) (1)
	all groups correctly connected for glutamic acid in both diagrams (1)
	glycine
only has three different groups / two groups are the same /
3-D diagram used to show symmetry (1)	8
	quality of written communication
for correct use and organisation of at least one technical term:
*(in the correct place), non-superimposable, enantiomer, stereoisomer(ism),
tetrahedral, assymetric (1)
[16]

 7.	

at least one correct skeletal formula (1)
correct cis and trans isomers of but-2-enal (1)	2
[2]
8.	(a)
 (1)	1
(b)	C=C double bond does not rotate (1)
	two different groups on each carbon (of the C=C) AW (1)	2
NOT on “each side” of the C=C
i.	trans because H / groups are on opposite sides AW (1)	1
ii.	any formula that shows the H on the same side – eg
 (1)	1
[5]
9.	H2N(CH2)6NH2 
ALLOW H2NCH2CH2CH2CH2CH2CH2NH2
	HOOC(CH2)8COOH 
ALLOW HOOCCH2CH2CH2CH2CH2CH2CH2CH2COOH
ALLOW CO2H for COOH
ALLOW acid chloride, ClOC(CH2)8COCl
ALLOW displayed formulae or skeletal formulae
[2]

10.	(i)

		2
(ii)	any valid suggestion to explain or describe stronger intermolecular
forces – e.g. Nomex is planar so packs together more easily /
greater H-bonding / Van der Waals’ / forces between molecules (1) AW
(ignore arguments based on Mr)	1
[3]

 11.	(i)	addition (polymerisation) (1)	1
NOT additional
(ii)
 (1)	1
(iii)	π-bond breaks (1)
	many molecules join / a long chain forms /
equation to show this using ‘n’ (1)	2
[4]

12.	(a)
	 (1)		

monomers connected by NHCO (1)
correct repeat shown (1)			
condensation	addition	(1) for both	
		4
(b)	HCl		1
 (c)		2
allow 1 mark for: both H3N+─(CH2)6─NH3+ and 
(d)	(i)	4	1
(ii)
 where R=H, CH3, CH2OH or CH2C6H5 (1)	1
(iii)	any three different chemically or biologically correct differences
between amino acids and the nylon monomers (1)(1)(1) - eg
•	protein monomers are amino acids / nylon monomers are a
(di)amine/base and a (di)acid
•	protein monomers have different types/R groups / nylon
monomers are two types/no variation
•	protein monomers have stereo/optical isomers/are chiral
•	protein monomers have higher melting points/
form zwitterions
	other possible answers include:
•	nylon monomers have longer chain length/no other functional
groups / no aromatic content / are symmetrical etc	3
don’t allow comparisons solubility or Mr
[12]

13.	(i)	equation

ALLOW
(CH3CO)2O + H2NC6H4OH → CH3CONHC6H4OH + CH3COOH
ALLOW

DO NOT ALLOW molecular formulae
2
(ii)	C10H11NO3 is
 
ALLOW amide shown as either CH3CONH– OR
H3CCONH– OR CH3COHN– OR H3CCOHN–
ALLOW ester shown as either –OCOCH3 OR –OOCCH3
1

(iii)	to ensure that there are no (harmful) side effects 
ALLOW impurities reduce effectiveness (of drug) OR might be toxic
OR avoids litigation OR harmful OR hazardous
ALLOW to ensure that the drug/active component is safe
IGNORE dangerous OR nasty OR can kill OR increased dosage
1
[4]

 14.	(i)	C13H20O3 (1)	1
(ii)	ketone (1)
ester (1)
alkene (1)	3
(iii)

both optical (1)
E/Z (1)	2
(iv)	possible side effects of other chiral compound (1)
increased costs/difficulty of separating of isomers (1)
using bacteria within synthetic route (1)	2 max
[8]

 15.	(a)	(i)	NaBH4 (1)	1
(ii)	4-hydroxypentanoic acid (1)	1
(b)	(i)	section of the polymer (1) – e.g.
	1
(ii)	a correct repeat shown (1) – e.g.
	1
allow ecf from (i) only if the repeat is every 2 carbons along the chain and has a COOH

(c)	(i)	C7H12O3 (1)	1
(ii)	C7H12O3 + 8½O2 → 7CO2 + 6H2O or ecf from (i))
formulae (1)
balancing (1)	2
(iii)	idea of providing oxygen /
reducing incomplete combustion AW (1)	1
 (d)	(i)	heat/warm/reflux (1)
NaOH / KOH(aq) (1)	2
(ii)	G is an ester / sensible argument based on polarity (1)	1
[11]
 
16.	(i)	a carbon with four different groups attached (1)
	a chiral carbon /centre (1)
	different spatial / 3-D arrangement (of the groups) (1)
	(stereo)isomers / mirror images are non-superimposable / molecules
are asymmetric (1)	3
ANY 3 out of 4 marks
(ii)	contains 2 chiral centres (1)
	each can have 2 (stereo)isomers/ 2×2 possibilities AW (1)	2
(iii)	use naturally occurring / enantiomerically pure amino acids
OR
use a stereospecific catalyst / enzyme / micro-organisms
OR
separate the mixture using a suitable method (1)	1
 
(iv)	higher doses are required (1)
	the drug /other stereoisomers may have (harmful) side-effects (1)	2
[8]