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BBHFDGNC
BBHFDGNC
C
[1]
2.
B
[1]
3.
C
[1]
4.
B
[1]
5.
(a)
(b)
boiling points increase (from the first member to the fifth member);
increasing size of molecule/area of contact/number of electrons (from
the first to the fifth member);
strength of intermolecular/van der Waals/London/dispersion forces
increase / more energy required to break the intermolecular bonds
(from first member to fifth member);
same general formula;
successive members differ by CH2;
same functional group / similar/same chemical properties;
gradual change in physical properties;
Accept specific physical property such as melting point, boiling
point only once.
2 max
[5]
IB Questionbank Chemistry
6.
A:
B:
C:
1,2-dichloroethane;
D:
5
[5]
7.
IB Questionbank Chemistry
8.
4
[4]
9.
Initiation:
UV/hf / hv / heat
Cl2 2Cl;
Reference to UV/hf/h/heat must be included.
Propagation:
Cl + CH4 CH3 + HCl;
CH3 + Cl2 CH3Cl + Cl;
Termination:
Cl + Cl Cl2 / CH3 + Cl CH3Cl / CH3 + CH3 C2H6;
Allow representation of radical without (e.g. Cl, CH3) if consistent
throughout mechanism.
If representation of radical (i.e. ) is inconsistent, penalize once only.
[4]
10.
(a)
(b)
but-1-ene;
Allow 1-butene.
CH3CH2CH=CH2;
IB Questionbank Chemistry
(c)
(d)
curly arrow going from C=C to Br of Br2 and curly arrow showing Br
atom leaving Br2 molecule;
representation of carbocation;
+
curly arrow going from lone pair/negative charge on Br to C ;
2
[9]
11.
12.
(CH3)2CHMgCl;
anhydrous / absence of water / ether solvent;
2
[2]
13.
(i)
IB Questionbank Chemistry
(ii)
1
[2]
14.
(a)
amine salt;
+
2
[4]
15.
D
[1]
16.
B
[1]
17.
A
[1]
18.
A
[1]
IB Questionbank Chemistry
19.
[5]
IB Questionbank Chemistry
20.
CH3CH2COOH + CH3OH
CH3CH2COOCH3 + H2O
[1] for reactants and [1] for products.
(concentrated) sulfuric acid/H2SO4;
+
4
[4]
21.
(i)
2
[6]
22.
5
[5]
IB Questionbank Chemistry
23.
curly arrow going from lone pair on O in H2O to carbonyl C and curly
arrow going from C=O bond to O;
Do not allow curly arrow originating on H in H2O.
representation of intermediate anion showing negative charge on
O and + on O of H2O;
Lone pair on O not required on representation of intermediate.
curly arrow going from lone pair/negative charge on O to CO to form
C=O and curly arrow showing Cl leaving and curly arrow from HO
+
bond to O ;
+
formation of organic product H3CCOOH and Cl and H /HCl;
4
[4]
24.
(a)
Allow curly arrow going from delocalized electrons in benzene to Cl for M1.
representation of carbocation with correct formula and positive charge on ring;
2
[62]
IB Questionbank Chemistry
25.
B
[1]
26.
D
[1]
27.
D
[1]
28.
C
[1]
29.
(i)
(ii)
(iii)
1
[6]
30.
(i)
(ii)
1
C3H8O + 4 2 O2 3CO2 + 4H2O / 2C3H8O + 9O2 6CO2 + 8H2O
Award [1] for correct products and reactants and [1] for correct
balancing.
Ignore state symbols.
+
IB Questionbank Chemistry
(iii)
5
[10]
31.
(a)
1,3-cyclohexadiene;
(b)
1
[2]
32.
For chloromethylbenzene:
electron deficient carbon on CH2Cl group making it susceptible to
nucleophilic attack;
For chlorobenzene:
steric hinderance / repulsion by electron cloud in benzene ring/CCl less polar;
CCl bond stronger;
2 max
Award [1] mark for either of the above.
[2]
33.
(a)
(i)
H3CCHClCH2I ;
(ii)
H3CC(OH)(CN)H;
IB Questionbank Chemistry
10
(iii)
1
(iv)
(b)
(CH3)2CHOH ;
CH3CHICH2Cl ;
(c)
Reaction
Type
(a) (i)
electrophilic addition;
(a) (ii)
nucleophilic addition;
(a) (iii)
addition-elimination;
(a) (iv)
Grignard;
4
[9]
IB Questionbank Chemistry
11
34.
Catalyst:
(concentrated) H3PO4/phosphoric acid/H2SO4/sulfuric acid;
Mechanism:
4
[4]
35.
Step 1:
H3PO4 /phosphoric acid / H2SO4 /sulfuric acid;
Product from step 1:
CH3CH2CH=CH2 /but-1-ene;
Step 2:
Br2 /bromine;
3
[3]
36.
B
[1]
37.
C
[1]
IB Questionbank Chemistry
12
38.
A
[1]
39.
B
[1]
40.
(a)
IB Questionbank Chemistry
13
(b)
(i)
HO to C bonded to Br;
IB Questionbank Chemistry
14
(ii)
+
in HO to C ;
If non-bonding pair not shown then arrow must originate from
negative sign on O or the minus sign.
Only penalize arrow from H once in (b).
If wrong formula is used for 2-bromo-2-methylbutane
award [2 max].
(iii)
(iv)
(v)
3 max
esterification / condensation;
CH3COO(CH2)4CH3 / CH3COO(CH2)4CH3 /
CH3COOCH2CH2CH2CH2CH3 /
2
Accept CH3COOC5H11
IB Questionbank Chemistry
15
(c)
elimination;
4
[21]
41.
(i)
nHO(CH2)5OH + nHOOCC6H4COOH
H[O(CH2)5OCOC6H4CO]nOH + (2n 1)H2O
3
Award [1] for correct reactants, [1] for correct polyester and
[1] for balanced water.
Award [3] if correct equation given for one molecule of diol
reacting with one molecule of dicarboxylic acid.
i.e.
HO(CH2)5OH + HOOCC6H4COOH HO(CH2)5OCOC6H4COOH + H2O
(ii)
1
[4]
42.
(a)
(i)
(ii)
1
Allow use of ortho and para notation.
IB Questionbank Chemistry
16
(b)
3
[5]
43.
4
[4]
44.
D
[1]
45.
B
[1]
46.
B
[1]
IB Questionbank Chemistry
17
47.
A
[1]
48.
(i)
(ii)
(iii)
49.
(i)
Step 1:
CH2CHCl + H2 CH3CH2Cl;
Step 2:
CH3CH2Cl + OH CH3CH2OH + Cl ;
IB Questionbank Chemistry
18
(ii)
(iii)
CH3COOH(aq) + H2O(l)
OR
CH3COOH(l) + H2O(l)
OR
CH3COOH(aq)
CH3COO (aq) + H (aq)
correct equation;
state symbols and
;
+
BL acid is CH3COOH and cb is CH3COO / BL acid is H3O and cb is H2O;3
[7]
50.
2 max
[2]
51.
(a)
(i)
A: butan-1-ol;
B: butan-2-ol;
C: (2-)methylpropan-2-ol;
D: (2-)methylpropan-1-ol;
Accept answers in the form of 1-butanol and 2-methyl-2-propanol etc.
Penalize incorrect punctuation, e.g. commas for hyphens, only once.4
(ii)
C/(2-)methylpropan-2-ol;
(iii)
A/butan-1-ol;
(iv)
B/butan-2-ol;
IB Questionbank Chemistry
19
(v)
1
(b)
(i)
SN2;
(ii)
3
[12]
52.
(a)
IB Questionbank Chemistry
20
(b)
(i)
(ii)
butan-2-ol/2-butanol;
CH3CH2CH(OH)CH3;
2-methylbutan-2-ol;
C2H5C(CH3)2OH;
2
[6]
53.
(i)
but-1-ene/1-butene;
(ii)
3
[4]
54.
(a)
(b)
(i)
2,3-dibromobutane;
IB Questionbank Chemistry
21
(ii)
2-bromobutane;
1
[3]
55.
showing curly arrow from double bond to H (in HBr) and curly arrow from bond in
HBr to Br;
showing the curly arrow from the lone pair/negative charge on Br to the secondary
carbocation and 2-bromobutane as correct product;
stating that the secondary carbocation will be formed in preference to the primary
carbocation;
the two positive/electron releasing inductive effects due to the two R groups on the
secondary carbocation make it more stable;
4
[4]
56.
(a)
(b)
1
[3]
IB Questionbank Chemistry
22
57.
D
[1]
58.
A
[1]
59.
D
[1]
60.
C
[1]
61.
(a)
(b)
A: l-bromobutane;
B: 2-bromobutane;
C: 2-bromo-2-methylpropane;
D: 1-bromo-2-methylpropane;
Penalize incorrect punctuation, e.g. commas for hyphens, only once.
Accept 2-bromomethylpropane and 1-bromomethylpropane for
C and D respectively.
(i)
(ii)
C/2-bromo-2-methylpropane;
unimolecular nucleophilic substitution;
+
RBr R + Br ;
Allow use of 2-bromo-2-methylpropane instead of RBr.
IB Questionbank Chemistry
23
(iii)
A/1-bromobutane/D/1-bromo-2-methylpropane;
(c)
(d)
(e)
(f)
respect to OH ;
Award [1] if correctly predicts no rate change for SN1 and
doubling of rate for SN2 of without suitable explanation.
2-bromobutane/B;
(plane-) polarized light shone through;
enantiomers rotate plane of plane-polarized light to left or right/
opposite directions (by same amount);
Accept turn instead of rotate but not bend/reflect.
physical properties identical (apart from effect on plane-polarized light);
chemical properties are identical (except with other chiral compounds);
Do not accept similar in place of identical.
(i)
elimination;
IB Questionbank Chemistry
24
(ii)
4 max
[25]
IB Questionbank Chemistry
25
62.
2
[2]
63.
showing curly arrows from benzene ring to CH3 and curly arrow from bond in
CH3I to catalyst;
+
4
[4]
64.
(i)
(ii)
3
[4]
65.
B
[1]
66.
A
[1]
IB Questionbank Chemistry
26
67.
B
[1]
68.
(i)
(ii)
Chloroethene:
(hydration of ethene for the manufacture of) ethanol/ C2H4 + H2O C2H5OH;
(synthesis of) CH3COOH /ethanoic/acetic acid;
(synthesis of) ethylene glycol/1,2-ethanediol/ethane-1,2-diol;
(synthesis of) drugs/pesticides;
(hydrogenation of unsaturated oils in the manufacture of) margarine;
Accept other commercial applications.
2 max
[5]
69.
(i)
IB Questionbank Chemistry
27
(ii)
and acidic/H ;
heat/reflux;
5
[7]
70.
(i)
CH3CH2CH2OH, propan-1-ol/1-propanol;
CH3CH(OH)CH , propan-2-ol/2-propanol;
Need both formula and name for mark.
Accept either condensed or full structural formulas.
CH3CH2CH2OH: primary and CH3CH(OH)CH3: secondary;
(ii)
CH3CH2CHO;
CH3CH2COOH;
CH3COCH3;
Accept either condensed or full structural formulas.
from propan-1-ol: CH3CH2CHO(propanal) obtained by distillation (as
product is formed);
propan-1-ol gives CH3CH2COOH (propanoic acid) by (heating under) reflux;
Award [1] if CH3CH2CHO and CH3CH2COOH identified but conditions
not given/incorrect.
propan-2-ol gives CH3COCH3 by heat / reflux;
5 max
[8]
IB Questionbank Chemistry
28
71.
4
[4]
IB Questionbank Chemistry
29
72.
curly arrow showing movement of electron pair from the double bond to
hydrogen in HBr;
formation of Br ;
OR
4 max
[4]
73.
2
[2]
IB Questionbank Chemistry
30
74.
Step 1:
H , heat
CH3CH2CH2CH2OH CH3CH2CH=CH2 + H2O;
5
[5]
75.
(a)
(b)
(c)
any pKa value or range of values within the range 2.87 4.86;
The actual pKa value is 3.98.
1
[5]
76.
A
[1]
77.
A
[1]
78.
B
[1]
IB Questionbank Chemistry
31
79.
B
[1]
80.
(a)
(b)
(i)
Cis(-1,3-dichlorocyclobutane)
Trans(-1,3-dichlorocyclobutane)
Need clear cis/trans structure and name for each mark.
Award [1] for 2 correct structures without names.
(ii)
81.
(i)
Accept CH3CH2CH2Br.
Penalize missing H atoms.
IB Questionbank Chemistry
Accept CH3CH2CH2CH2NH2.
1
32
(ii)
4
[5]
82.
(i)
hot;
alcoholic OH /NaOH/KOH;
C2H5Br + C2H5ONa C2H4 + NaBr + C2H5OH /
C2H5Br + NaOH C2H4 + NaBr + H2O;
IB Questionbank Chemistry
33
(ii)
originating on H in OH .
5
[8]
83.
(a)
IB Questionbank Chemistry
34
(b)
4
[5]
84.
(a)
IB Questionbank Chemistry
35
85.
3
[3]
86.
B
[1]
87.
A
[1]
88.
C
[1]
89.
B
[1]
90.
(a)
(b)
methylpropene;
Accept 2-methylpropene.
(i)
IB Questionbank Chemistry
36
(ii)
Award [1] if structure and correct name are given for 2-bromo-2methylpropan-1-ol.
2
[4]
91.
(i)
(ii)
2 max
addition;
(iii)
(iv)
monomers are smaller molecules / have smaller surface area than polymers;
Accept monomers have lower molecular mass.
with weaker intermolecular/Van der Waals/London/dispersion forces;
Accept opposite argument for polymers.
2
[6]
IB Questionbank Chemistry
37
92.
chloroethane;
(electrophilic) addition;
Do not accept free radical/nucleophilic addition.
2
[2]
93.
81.7
18.3
nC = 12.01 = 6.80 and nH = 1.01 = 18.1;
ratio of 1: 2.67 /1: 2.7;
C3H8;
No penalty for using 12 and 1.
(b)
C3H8;
(c)
(i)
(a)
(ii)
Br2 /bromine;
UV/ultraviolet light;
Accept hf/hv/sunlight.
2
2
+
(d)
Initiation:
Br2 2Br;
Propagation:
Br + RCH3 HBr + RCH2;
RCH2 + Br2 RCH2Br + Br;
Termination: [1 max]
Br + Br Br2;
RCH2 + Br RCH2Br;
RCH2 + RCH2 RCH2CH2R;
Award [1] for any termination step.
Accept radical with or without throughout.
Do not penalize the use of an incorrect alkane in the mechanism.
(e)
(i)
IB Questionbank Chemistry
4 max
38
(ii)
3
[16]
94.
(i)
(ii)
CH3OCH2CH;
CH3CHOHCH;
Allow more detailed structural formulas.
95.
(a)
IB Questionbank Chemistry
3 max
39
(b)
2 max
[5]
96.
(a)
A: CH3CH2CH(CH3)Br;
(b)
1
[2]
97.
4
[4]
98.
4
[4]
99.
(a)
phenol;
negative charge/lone pair on oxygen can interact with delocalized
electrons of benzene/aromatic ring so spreads out charge more / OWTTE; 2
IB Questionbank Chemistry
40
(b)
chloroethanoic acid;
chlorine (atoms) withdraws electrons from OH bond, making it
+
break more easily to release H ions / electron-withdrawing nature
of chlorine / greater electronegativity of chlorine / OWTTE;
3
[5]
100. D
[1]
101. B
[1]
102. B
[1]
103. C
[1]
104. (a)
(b)
(i)
IB Questionbank Chemistry
41
(ii)
(iii)
0.2(0);
1
min ;
2-bromo-2-methyl-propane;
Do not penalize missing hyphens or added spaces.
Accept 2-bromomethylpropane.
tertiary (structure);
(iv)
2
[11]
105.
curly arrow going from delocalized electrons in benzene to Cl in Cl2 and curly
arrow going from ClCl bond to AlCl3;
Do not penalize if curly arrow originates inside circle.
+
Allow curly arrow going from delocalized electrons in benzene to Cl for M1.
representation of carbocation with correct formula and positive charge on ring;
curly arrow going from lone pair/negative charge on Cl in AlCl4 to H and curly
arrow going from CH bond to benzene ring;
+
Allow H + AlCl4 HCl + AlCl3 as alternative to curly arrow going from lone
4
[4]
IB Questionbank Chemistry
42
3
[3]
107. (a)
CH3CONHCH2CH3;
+
CH3CH2NH3 Cl /CH3CH2NH3Cl;
Order of E and F does not matter.
(b)
CH3CH2NH2 / ethylamine;
(c)
addition-elimination;
Accept acylation.
1
[4]
108. A
[1]
109. C
[1]
110. C
[1]
111. A
[1]
IB Questionbank Chemistry
43
112. (i)
(ii)
(iii)
3
(iv)
1
(v)
secondary (alcohol);
propanone / acetone;
2
[12]
113. (i)
(ii)
IB Questionbank Chemistry
44
(iii)
2
[8]
114. (a)
planar;
all bond angles are 120/the same;
2
Accept all carbons are sp hybridization.
(b)
4 max
1
[5]
IB Questionbank Chemistry
45
115. (i)
(ii)
116. (i)
(ii)
[3]
IB Questionbank Chemistry
46
117.
IB Questionbank Chemistry
47
118.
4
[4]
119. C
[1]
120. D
[1]
121. B
[1]
IB Questionbank Chemistry
48
122. B
[1]
123. D
[1]
124. (a)
(i)
alcoholic NaOH/OH ;
reflux / heat;
Penalize missing Hs once only throughout the question
(ii)
elimination reaction;
Then accept either E1 or E2 mechanism.
E1
IB Questionbank Chemistry
49
(iii)
(iv)
(b)
Award [1] for correct structure and [1] for correct 3-D
representation of both enantiomers.
(i)
(ii)
(iii)
125. (i)
(ii)
amide / peptide;
H2N(CH2)6NH2;
HOOC(CH2)8COOH / ClOC(CH2)8COCl;
IB Questionbank Chemistry
50
(iii)
nHOOCC6H4COOH + nHOCH2CH2OH
HO--(--OCC6H4COOCH2CH2O--)nH + (2n 1)H2O;
Award [1] for correct organic product and [1] for (2n 1)H2O.
Accept --(--OCC6H4COOCH2CH2O--)n for the organic product.
2
[5]
126. (i)
IB Questionbank Chemistry
51
(ii)
3
[5]
IB Questionbank Chemistry
52
127.
3
[3]
128. (i)
reaction with Br2 and UV light (to react with methyl group);
Br2 and AlBr3 / AlCl3 (to substitute in benzene ring);
Accept in either order.
(ii)
[4]
129. D
[1]
130. C
[1]
131. A
[1]
132. C
IB Questionbank Chemistry
53
[1]
133. (i)
(ii)
(iii)
(iv)
(v)
(vi)
Bonds broken
(1)(CC) + (1)(OH) + (5)(CH) + (1)(CO) + (3)(O=O)
= (1)(347) + (1)(464) + (5)(413) + (1)(358) + (3)(498) = 4728(kJ);
Bonds formed
(2 2)(C=O) + (3 2)(OH)
= (4)(746) + (6)(464) = 5768 (kJ);
1
H = 4728 5768 = 1040 kJ mol / 1040 kJ;
Units needed for last mark.
Award [3] for final correct answer.
Award [2] for +1040 kJ.
A: CH3CHO;
B: CH3COOH/CH3CO2H;
Accept either full or condensed structural formulas but not the
names or molecular formulas.
A: distillation;
B: reflux;
ethanol/CH3CH2OH;
hydrogen bonding (in ethanol);
Award second point only if the first is obtained.
134. (i)
(2-)methylbutane / (2,2-)dimethylpropane;
IB Questionbank Chemistry
54
(ii)
curly arrow going from O/lone pair of OH (but not H) to the C attached to Br;
leaving of Br;
transition state representation with both Br and OH attached to C1;
135. (a)
bonding electron pair spread over three (or more) nuclei or atoms/
not restricted/confined between two nuclei or atoms / OWTTE;
IB Questionbank Chemistry
55
(b)
( H/proton) NMR spectrum shows only one peak / all the Hs in the
same chemical environment;
not 2 peaks / not 2 different chemical environments;
OR
electron density maps;
show even electron density over ring;
chemical evidence [2 marks]:
hydrogenation of C6H6 (1,3,5-cyclohexatriene) expected to
produce three times as much energy as cyclohexene;
benzene produces less (due to delocalization);
OR
benzene undergoes substitution rather than addition reactions;
as it is more stable (due to delocalization);
OR
enthalpy of combustion of C6H6 less than expected;
different bond energies;
4 max
[5]
IB Questionbank Chemistry
56
3 max
[3]
5
[5]
138.
2
[2]
IB Questionbank Chemistry
57
139. (a)
(b)
3 max
[5]
140. B
[1]
141. A
[1]
142. C
[1]
143. D
[1]
IB Questionbank Chemistry
58
144. A: CH3CHO;
B: CH3COOH/CH3CO2H;
Accept either full or condensed structural formulas but not the names
or molecular formulas.
A: distillation;
B: reflux;
4
[4]
2
[2]
146. (i)
CH 3 CH 2 OH
K 2Cr2 O 7
CH3CH2OH CH3COOH CH3CH2CH2CH3 + H2O
H+
H2SO4
manganate (VII)/MnO4 .
+
IB Questionbank Chemistry
59
(ii)
K 2Cr2 O 7
H 2O
H2C=CH(CH3) CH3CH(OH)CH3 (CH3)2CO
H+
H2SO4(conc.)
dichromate/Na2Cr2O7 / dichromate/Cr2O7
/ potassium manganate(VII)/
147.
Allow the curly arrow to originate from either the lone pair or O of OCH2CH3 but
3
[3]
IB Questionbank Chemistry
60
148. (i)
compounds with the same (molecular formula and) structural formula but
different arrangements of atoms in space / OWTTE;
1
(ii)
Allow [1 max] if the structures are correct but it is not clear that they are
mirror images.
2
[3]
5
[5]
IB Questionbank Chemistry
61
5
[5]
151. C
[1]
152. A
[1]
153. D
[1]
154. C
[1]
155. (a)
(i)
Isomer
Boiling point
36 C
28 C
10 C
IB Questionbank Chemistry
62
(ii)
(b)
B: 2-methylbutane/methylbutane;
C: 2,2-dimethyl propane/dimethyl propane;
Do not penalize missing commas, hyphens or added spaces.
Do not accept 2-dimethylpropane, or 2,2-methylpropane.
C5H12;
Accept any two of the following explanations.
C5H11OH has greater molar mass / produces less grams of CO2 and
H2O per gram of the compound / suitable calculations to show this;
C5H11OH contains an O atom which contributes nothing to the energy
released / partially oxidized / OWTTE;
analogous compounds such as butane and butan-1-ol show a lower
value for the alcohol per mole in the data book / OWTTE;
the total bond strength in the pentanol molecule is higher than the total
bond strength in pentane;
the total amount of energy produced in bond formation of the products
per mole is the same;
fewer moles of pentanol in 1 g;
pentanol requires more energy to break intermolecular forces/
hydrogen bonding / OWTTE;
3 max
[8]
156. (i)
(ii)
(iii)
(substitution)
nucleophilic;
unimolecular / OWTTE;
1-chlorobutane:
SN2;
2-chloro-2-methylpropane:
SN1;
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63
(iv)
+
curly arrow from lone pair or negative charge on O in OH to C ;
6
[11]
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64
157. (i)
CH3CH2CH2CHO / (CH3)2CHCHO;
CH3CH2CH2COOH / (CH3)2CHCOOH;
(iii)
CH3CH2COCH3;
(iv)
orange to green;
(ii)
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65
(v)
1
[9]
158. (a)
(b)
dimethylamine / (CH3)2NH;
2 max
[3]
2
[2]
OR
CH3Cl + NaCN CH3CN + NaCl;
+
2 max
[2]
161. (a)
(i)
A: CH3CH2C(CH3)2OH;
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66
(ii)
1
(b)
addition-elimination / condensation;
1
[3]
162.
curly arrow from C=C to H of HI and curly arrow showing iodide leaving;
structure of carbocation and iodide attacking carbocation from either lone pair or
negative charge;
+
Allow CH3C HCH2CH3.
structure of CH3CHI(CH2CH3) as major organic product (C);
secondary/ 2 carbocation more stable than primary/1 carbocation;
because it is stabilized by a greater number of electron-releasing alkyl groups;
Award [3 max] for a correct mechanism involving the formation of the
1-iodo product.
5
[5]
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67
163.
5
[5]
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68
164. A
[1]
165. C
[1]
166. D
[1]
167. B
[1]
168. (i)
2
(ii)
(iii)
[5]
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69
169. (i)
(ii)
1
[4]
170. (i)
SN2;
(ii)
2
[6]
171. (i)
CH3CH2Br + OH CH3CH2OH + Br ;
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4 max
70
(ii)
(iii)
addition;
1
[9]
3
[3]
173. (i)
activating;
(ii)
(iii)
2
[4]
174. B
[1]
175. C
[1]
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71
176. A
[1]
177. B
[1]
178. A
[1]
179. (a)
2
Allow condensed structural formulas such as
CH3CH2CH2CH2OH.
Award [2] for all three correct isomers, [1] for any two
correct isomers.
[5]
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72
180. (i)
H
H
(iii)
Ester;
Arene/benzene ring;
Alcohol;
Award [2] for any three correct, award [1] for any two
correct.
Do not accept alkane as a type of functional group in this
molecule.
[6]
181. (i)
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73
(ii)
hv / UV light
CH4 + Cl2 CH3Cl + HCl;
182. (i)
A. = CH3(CH2)7CHO;
B. = CH3(CH2)7COOH/CH3(CH2)7CO2H;
C. = (CH3)3COH;
D. = (CH3)2CO;
E. = BrCH2CH2Br;
addition;
/-(CH2-CH2)3-/-(CH2)6-;
2
[7]
183. D
[1]
184. B
[1]
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74
185. D
[1]
186. C
[1]
187. (a)
Cl
Cl
a n d 1 ,1 d ic h lo r o c y c lo p r o p a n e ;
Cl
Cl
Cl
Cl
Cl
C l
Cl
C l
2
Cl
CH
C l
C l
C H
C l
and
H
Cl
C l
C H 2Cl
and
H
CH 2C l
2
[4]
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75
188. (i)
O H
O H
C
C H 3CH
C H
CH
CH 2C H
(iii)
CH
CH
CH
;
H
H
C
;
CH
(iv)
3 max
3
[3]
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76
190. (a)
(b)
H 3C
CN
H 3C
CN
O
:C N
H 3C
H 3C
C H 3
Suitable diagram with
+
curly arrow showing attack by :CN on carbonyl C ;
curly arrow showing pi bond breaking;
+
curly arrow from :O to H ;
structure of product (CH3)2C(OH)CN;
C
C H
O H
3
(c)
191. (a)
(b)
(i)
(ii)
delocalized electrons;
1
[5]
192. (a)
addition-elimination/condensation;
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77
(b)
H
N
N O
+ H 2O ;
N O
1
[4]
4
[4]
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78