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HALOGENOLALKANES AND ALCOHOLS HW MS
1.	

dipoles	1
hydrogen bond between O in one O-H
and H in the other O-H	1
lone pair from O involved in the H-bond	1
[3]

 2.	C_6H_12O_6 ® 2C_2H_5OH + 2CO_2
(C_2H_5OH & CO_2 )
[2]
 
3.	(a)	C_2H_5OH + 3O_2 ® 2CO_2 + 3H_2O 	2
2CO_2 + 3H_2O gets 1 mark
(b)	Fermentation	1
C_6H_12O_6 ® 2C_2H_5OH + 2CO_2  	1
Yeast /enzyme / temperature about 30 °C/ batch process 	1
Hydration of ethene. 	1
C_2H_4 + H_2O ® C_2H_5OH 	1
Temp > 100 °C/Press 370 - 100 atm	/ 6 -20 MPa/phosphoric acid catalyst/
continuous process 	1
Glucose is obtained from plants 	1
Ethene is obtained from crude oil/cracking/fossil fuel 	1
glucose is renewable/ethene isn’t 	1
1 mark available for Quality of written communication….. base the award
of the mark on the ability to communicate the essential chemistry by correct
use of at least two from:
fermentation/hydration/catalyst/renewable/sustainable/biofuel/
enzymes/finite/cracking 	1
[12]

4.	identifies the three process as cracking, reforming, isomerisation	1
recognises the need for high temperature or a catalyst	1
equation for cracking	1
equation for isomerisation	1
state that reforming converts chains into rings/cyclic compounds	1
equation for reforming (balanced with H_2 could score two marks)	1
oil is finite/non-renewable	1
ethanol is renewable/sustainable	1
from plants/crops/sugar cane/sugar beet/glucose/sugar/ fermentation	1
C_2H_5OH + 3O_2 ® 2CO_2 + 3H_2O	1
QWC
·	organise relevant information clearly and coherently, using specialist
vocabulary when appropriate (minimum of 4 from cracking/
isomerisation/ reforming/ renewable/ feedstock/
finite/fermentation/non-renewable/sustainable/zeolite/bimetallic
catayst/ etc )
·	reasonable spelling, punctuation and grammar throughout	1
[11]

5.	CH_3CH(OH)CH_3 + 4½O_2 ® 3CO_2 + 4H_2O /C_3H_8O
(1 mark if correct formula for all four chemicals and 1 mark for correct balancing)
[2]

6.	(a)	(i)	C_4H_10 	1
(ii)	C_2H_5O 	1
(iii)	B and E 	1
(iv)	A and F 	1
(b)	(C_4H_9OH ®) C_4H_8 + H_2O 	1
(c)	any unambiguous formula: 	1

CH_2CHCHCH_2
buta-1,3-diene 	1
name ecf to the structure only if structure above has formula C_4H_6
[7]
7.	(a)	(i)	reaction 1	1
(ii)	reaction 4	1
(iii)	reaction 3	1
(b)	(i)	lone pair/electron pair donor	1

	Correct dipole	1
	Curly arrow from the O in the OH^- to C in the CH_2	1
	Curly arrow to show movement of bonded pair in the C-Cl bond	1
	Cl^- as a product	1
(c)	(i)	same molecular formula , different structure/arrangement of atoms.	2
(same formula, different structure.)
(ii)		2
				
 (d)	(i)	addition, (not additional)	1
(ii)	poly(propene)/ polypropene/ polypro-1-ene, polypropylene	1
(iii)		1

[15]

8.	(a)	(i)		1

(ii)	H_2SO_4/Al_2O_3/(hot) pumice/H_3PO_4	1
(H_2SO_4(aq) or dil H_2SO_4 loses the mark)
(iii)		1

C_6H_11OH / C_6H_12O ® C_6H_10 + H_2O
(b)	(i)		1

(ii)		2

[6]

9.	(i)	butan-2-ol by name or by formula 	1
(ii)	

curly arrow from the O of the OH- to C^(δ+) 
curly arrow from C-Cl bond to Cl and correct dipoles 
correct products/ allow NaCl 
curly arrow from lone pair on :OH^- 
	S_N1 route can still score all 4 marks:
curly arrow from C-Cl bond to Cl and correct dipoles 
curly arrow from the O of the OH^− to C+ ion 
correct products/ allow NaCl 
curly arrow from lone pair on :OH^− 	4
[5]

10.	(a)	Cl ^− must be shown as a product 	1
(at least 1) lone pair of electrons on the O in the OH ^− with curly arrow
from the lone pair on the OH ^− to the C(^d+)	1
dipoles on the C-Cl bond 	1
curly arrow from C-Cl bond to the Cl^d− 	1
The mechanism below would get all 4 marks.

(b)	(i)	mark for method/dividing by A_r / C, 3.15; H, 6.3; Cl, 1.58. 	1
	divide by smallest to get C_2H_4Cl 	1
	alternative method:
	% of each element  x 127 ¸ A_r of that
element = molecular formula, hence deduce empirical formula
(ii)	C_4H_8Cl_2 	1
(iii)	any unambiguous form of: 
	
		1
(iv)	any unambiguous form of: 

		1
ecf to (iii) provided that there are two OHs in (iii)
[9]

11.	(i)	M_r of 2-methylpropan-1-ol = 74	1
moles = 4.44/74 = 0.06	1
(ii)	moles = 5.48/137 = 0.04	1
(iii)	66.7%	1
[4]

12.	(i)	1

require an attempt at a 3D structure and
bond angles must clearly not be 90°.
require at least one ‘wedge’ bond or one
‘dotted’ bond
(ii)	108 - 111°	1
(iii)	volatile/low boiling/gas/non-toxic/non-flammable/unreactive/liquefied under pressure/inert	1
(iv)	homolytic = bonded pair split equally/ each retains 1 electron	1
fission = bond breaking	1
(v)	C-Cl (no mark) because it is the weaker bond	1
(vi)	Cl·	1
·CF_3 (allow CF_3·)	1
(lack of ‘dots’ penalise once)
[8]

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