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AS CHEMISTRY
CHEMISTRY TEST.
TOPIC:- ORGANIC CHEMISTRY
TOTAL MARKS:-40
Note:- Databooklet page is given at the end of this paper.

NAME:__________________________________________________________

(1) C
 alciumlactateisusedinsomemedicines.Itformswhenlacticacid(2-hydroxypropanoicacid)
reactswithcalciumcarbonate.
OH

H 3C C H

CO2H
lactic acid

(i) Identify the twootherproductsofthereactionoflacticacidwithcalciumcarbonate.

.......................................................................................................................................[1]

Twopossiblemethodsofmakinglacticacidareshown.

O OH
reaction 1
C H3C C H
H 3C H reaction 2
CN
OH

H 3C C H

CO2H
OH O lactic acid
reaction 3 reaction 4
H3C C H C
H 3C CO2H
CH2OH

(ii) Statesuitablereagentsandconditionsforreactions1 and 3.

reaction reagents and conditions

[4]
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2 Cyclohexaneisacolourlessliquidusedinindustrytoproducesyntheticfibres.

 Areactionschemeinvolvingcyclohexaneisshown.

Cl
reaction 1 reaction 2

(a) Reaction 1involvesafreeradicalsubstitutionmechanism.

(i) Statetheessentialconditionrequiredforreaction1 to occur.

.......................................................................................................................................[1]

(ii) Completethetabletogivedetailsofthemechanisminreaction1.

nameofstep reaction

................................. Cl 2 2Cl •

•
propagation + Cl • +
..............................

Cl
•
................................. + Cl 2 + Cl •

•
termination + Cl •
..............................

 [4]

(b) Namethetypeofreactionthatoccursinreaction2.

..............................................................................................................................................[1]
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3 (a) A series of reactions starting from 1-bromobutane is shown.

HCN and KCN reaction 1

1-bromobutane P CH3(CH2)3CO2H

OH–(aq) reaction 2

polymer
but-1-ene
Q
R

(i) Draw the displayed formula of compound P.

[1]

(ii) Identify the reagent(s) and conditions for reactions 1 and 2.

reaction 1 ............................................................................................................................

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

(iii) Draw the structure of the repeat unit of polymer Q.

[2]
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(b) Complete the reaction scheme to show the mechanism of the reaction of 1-bromobutane with
OH–(aq) to produce R.

Include all necessary charges, dipoles, lone pairs and curly arrows and the structure of R.

CH3CH2CH2

H C Br

–
OH

[3]

(c) But-1-ene reacts with steam as shown to form a mixture of two structural isomers, S and T.

reflux
S U
Cr2O72– / H+
major product
but-1-ene + steam

minor product

S can be oxidised with acidified potassium dichromate(VI) to form compound U.

S and U both react with alkaline aqueous iodine.

(i) Identify the type of reaction that occurs when but-1-ene reacts with steam.

....................................................................................................................................... [1]

(ii) State what can be deduced about the structure of S from its reaction with alkaline aqueous
iodine.

....................................................................................................................................... [1]
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(iii) Explain why S is the major product of the reaction of but-1-ene with steam.

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

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

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

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

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

(iv) Draw the skeletal formulae of S, T and U.

S T

U
[3]

(v) Write an equation to represent the oxidation of S to U by acidified potassium dichromate(VI).

You should use [O] to represent the oxidising agent.

....................................................................................................................................... [1]
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4 The following compounds were all found to be components of a sample of petrol.

H CH3

CH3(CH2)2CH3 (CH3)3CCH2CH(CH3)2 H 3C C C OH

H 3C H

G H J

(a) (i) Give the molecular formula of compound G.

....................................................................................................................................... [1]

(ii) Give the empirical formula of compound H.

....................................................................................................................................... [1]

(iii) Draw the skeletal formula of compound J.

[1]

(b) Write an equation to represent the complete combustion of compound H.

.............................................................................................................................................. [1]

(c) Fossil fuels are often contaminated with sulfur.

State and explain why supplies of fossil fuels that contain sulfur pose a problem to the
environment.

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

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

.............................................................................................................................................. [2]
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5 Some reactions of compound P, C5H8O, are shown.

compound Q

H2(g)
Ni(s) catalyst

O cold, acidified
NaBH4 KMnO4(aq)
compound R compound S
compound P

OH–(aq)
I2(aq)

O
compound T +
–
O

(a) (i) Give the structures for organic compounds Q, R, S and T.

R S

[4]
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(ii) Give the systematic name of compound P.

....................................................................................................................................... [1]

(iii) What would you observe when compound P is reacted with 2,4-dinitrophenylhydrazine
(2,4-DNPH)?

....................................................................................................................................... [1]

(b) Compound U contains a chiral centre and has the same molecular formula as compound P,
C5H8O.

• Compound U readily decolourises a sample of bromine water.

• Compound U does not show cis-trans isomerism.
• When compound U is heated under reflux in the presence of excess acidified
potassium dichromate(VI), the organic product gives the infra-red spectrum shown.

infra-red spectrum of product

100

transmittance /
%
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

Use the information given to suggest a structure for compound U.

Explain your answer.

[4]

[Total: 10]

[Turn over
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8 Characteristic infra-red absorption frequencies for some selected
bonds

Functional groups containing Absorption range (in Appearance of peak

Bond
the bond wavenumbers)/cm–1 (s = strong, w = weak)
C−O alcohols, ethers, esters 1040–1300 s
C=C aromatic compounds, alkenes 1500–1680 w unless conjugated
amides 1640–1690 s
C=O ketones and aldehydes 1670–1740 s
esters 1710–1750 s
C≡C alkynes 2150–2250 w unless conjugated
C≡N nitriles 2200–2250 w
alkanes, CH2−H 2850–2950 s
C−H
alkenes/arenes, =C−H 3000–3100 w
N−H amines, amides 3300–3500 w
carboxylic acids, RCO2−H 2500–3000 s and very broad
O−H H-bonded alcohol, RO−H 3200–3600 s
free alcohol, RO−H 3580–3650 s and sharp