SMK TENGKU INTAN ZAHARAH 23000 UNGUN TERENGGANU

MARKING SCHEME
SUMMATI!E ASSESSMENT THIR TERM ST"M 20#3

CHEMISTRY One hour and a half hours

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STPM CHEMISTRY 962/2 MARKING SCHEME SECTION A

Question No. $

Answer C

E !"#n#tion This compound has one chiral carbon with four different groups. Thus it can show optical isomers. COOH | C CH3 NH2 COOH | C H NH2

H3C

Phenol reacts with bromine water to produce a white precipitate. OH OH

Room temp

Br $ 3Br2 a!"

Br

Br 2# $# %&tribromophenol white precipitate" whereas phen'lmethanol water CH2OH does not react with bromine

The reaction between methane and chlorine in the presence of light in(ol(es a free radical mechanism. The propagation step is Cl ) CH$ Cl2 ) CH3 HCl ) CH3 CH3Cl ) Cl

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Question No. Answer E !"#n#tion

% & ) & CH2Br answer *" and

& O C CH3 answer C" are susceptible to ) nucleophilic attac+ because the carbon atom in these carries a partial positi(e charge# CH 3 is susceptible to free radical substitution reactions. Ben,ene ring answer B" and carbon&carbon double bonds contain electrons. Hence# the' are susceptible to electrophilic attac+. Re&e&'er ( The electron densit' of an electrophile is (er' low. Therefore# it will attac+ an electron rich centre# such as# the ben,ene ring since the electron densit' is (er' high in the ben,ene ring. OH OH Cl Cl ) 3Cl2 ) 3HCl Cl 2# $# % - trichlorophenol

'

% 6

Phenol undergoes electrophilic substitution. O Cl || | CH3 C CH ) PCl. CH3 C CH3 ) POCl3 | Cl /ster produces alcohol and carbo0'lic acid when acidic h'drol'sis is performed. CH3 CH2"2$COO CH2"21CH3 ) H2O CH3 CH2"2$ COOH ) CH3 CH2"21OH Carbo0'lic acid *lcohol

Remember2 The amino group acti(ates the ben,ene ring towards substitution# at the ortho and para positions. Therefore# bromine will replace h'drogen at the ortho and para positions.

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Question No. 9 $* A The pol'mer is produced from the addition pol'merisation reaction. 3olecules with double bonds are 4oined together to form a long chain of the pol'mer. Answer E !"#n#tion Carbon'l group is found in aldeh'des and +etones.

$$ $2

)#* 2* 3+

Optical isomers are onl' different in the aspect of polari,ed light rotation.

Butan&2&ol is a secondar' alcohol. O0idation of the alcohol produces a A +etone. )# onl,+ H H H | | | CH3 C C CH3 ) 5O6 CH3 C C CH3 ) H2O | | | || H OH H O Butanone )#* 2* 3+ The C 7 C undergoes electrophilic addition. The carbon'l group undergoes nucleophilic addition. The ben,ene ring undergoes electrophilic substitution. The particular pol'mer can be drawn as follows...

$%

$&

%)#*2+

Thus this pol'mer can be s'nthesised from

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Question No. Answer E !"#n#tion

This pol'mer is pol'amide because it contains

The group in this molecule ma+es it a pol'ester. 8t is not resistant against al+aline h'drol'sis because esters and amides can easil' be h'drol'sed. $' A)#+ Pol' 2&meth'lbuta&l #3&diene" CH3 & &CH2&C7CH&CH2"n is unsaturated# with C7C double bond and can be o0idised b' 3nO$& 9H). Pol' ethene" and pol' phen'lethene" are saturated# cannot be o0idised. 5:TP3 2;<;6

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STPM CHEMISTRY 962/2 MARKING SCHEME SECTION + , Stru-ture. Question /
Q0ESTION NO S0GGESTE1 ANS2ERS MARK

<% a" i" < )-+ &%r $ NH3

/thanol

N$

$ .%r/

<% a" ii" )CH3+2C%r2 $ NaOH =% a" iii" /CHO CH3/ C / CH3 O <

i" CH3CH23gBr ii" H3O)

CH/CH2CH3 OH

<

<% b" i"

Na)O&

CH2CHCH3 O&Na)

<

<% b" ii"

Na)O&

CH2CCH3 OH

<

<% b" iii"

CH83
<% b" i("

and

Na)O&

O > CH2?C?O&Na)

<

HO
TOTA3

COOH

<

) MARKS

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Q0ESTION NO S0GGESTE1 ANS2ERS MARK

<@ a" i" <@ a" ii"

*n electrophile is an electron deficient species which accepts a lone pair electrons from another species to form a coordinate bond# /lectrophile are Aewis acids CH27CH2 ) Br2 B BrCH2&CH2Br

< 2

<@ b" i"

C2

HOCH2CH CH3"OH or HOOCCH2CH2COOH

< < < < < Total E mar+s

D 2 CH27C CH3"COOCH3 <@ b" ii"

Pol'mer C2 Condensation pol'meri,ation Pol'mer D2 *ddition pol'merisation

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SECTION C ,Ess#4 Question/ Q0ESTIO N NO <E a" S0GGESTE1 ANS2ERS 2&butanol Optical isomerism. 8t has a chiral carbon atom bonded to four different groups. 8t has a pair of enantiomers that are non superimposable mirror images. S0GGESTE 1 MARKS < < <

OH CH3 H3CH2C C H 3irror plane H

OH

CH3 CH2CH3

Butenedioic acid geometrical isomerism This isomerism arises due to restricted rotation about the C7C bond. HOOC COOH HOOC H H C 7 C COOH Trans& butenedioic

< <

<

C 7 C H H Cis& butenedioic acid acid

<E b"

3olecular formula 2 C.H<2O P 2 CH3CH2CH2CH OH"CH3 O > F 2 CH3CH2CH2CCH3 CH3CH2CH2CH OH"CH3 ) 5O6 B CH3CH2CH2COCH3

P is an alcohol with the CH3CH OH" - group which reacts with

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Q0ESTIO N NO S0GGESTE1 ANS2ERS S0GGESTE 1 MARKS

al+aline iodine to produce CH83. CH3CH2CH2CH OH"CH3 ) $82 ) OH& B CH3CH2CH2COO& ) CH83 ) .H8 F is a +etone with the CH3CO&" which reacts with al+aline iodine to produce CH83. CH3CH2CH2COCH3 ) 382 ) OH& B CH3CH2CH2COO& ) CH83 ) 3H8 F ia a carbon'l compound which forms a precipitate with 2#$ dinitrophen'lh'dra,ine. O2N ) H2NNH NO2

CH3CH2CH2COCH3

NO2 ) H2O

O2N CH3CH2CH2C7NNH G CH3

Total 19(a)(i)
H HO2/ $ CH3CH2?C?Cl H CH3CH2 HO? C ? Cl H H & H CH3CH2?C?OH ) Cl& H

<. mar+s

#$#

%-&ole0ular nu0leo1h-l-0 su's2-2u2-on :N2" 19(a)(ii) The ra2e of rea02-on -n0reases because 2he 'rea3-n4 of C/%r 'ond needs less ener4, 2han 2ha2 of C/Cl 'ond. This is due to 2he len42h of C/%r 'ond -s less 2han 2he C/Cl 'ond len42h &a3-n4 -2 5ea3er and eas-er 2o 'rea36 # # #

CH3CH2CH2Cl ) NaOH
<E;HC

reflu0

CH3CH2CH2OH ) NaCl

CH3CH2CH2OH conc. H2:O$ CH3CH7 CH2 CH3CH7 CH2 ) HCl CH3CHClCH3

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Q0ESTIO N NO 19(b)(i) S0GGESTE1 ANS2ERS S0GGESTE 1 MARKS #$# #$# # 19(b)(ii) Catal'tic crac+ing is used 2o 1ro7-de e82ra 1e2rol and as a sour0e of al3enes for 2he &anufa02ure of &an, 1e2ro0he&-0als6 19(b)(iii) Catal'tic crac+ing is carried out at .90:C using the 0a2al,s2s s-l-0on )I!+ o8-de and alu&-n-u& o8-de6 # # #9 MARKS Correct steps <m < m for correct reagent and condition of each step." <$<$<" m # #

TOTA;
2; a" *dd solid phosphorous I" chloride to ethanol at room temperature. C2H.OH $ PCl. C2H.Cl3 $ HCl

Bubbled chloroethane into hot potassium c'anide dissol(ed in ethanol. C2H.Cl $ JCN C2 H.CN $ JCl

Boiling propanenitrile with dilute sulphuric acid. C2H.CN $ 2H2O $ H$ 2; b" C2H.COOH $ NH$ $ Correct steps <m < m for correct reagent and condition of each step." <$<" m

Heat </propanol with e0cess of concentrated sulphuric acid at <E; o C. CH3CH2CH2OH CH3 CH 7 CH2 $ H2O

Pass propene together with steam o(er heated phosphoric acid adsorbed on the surface of silicon dio0ide". CH3 CH CH2 ) H2O CH3 CH OH 2; c" Boiling 2/bromopropane with a!ueous sodium h'dro0ide. CH3

Correct steps

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Q0ESTIO N NO CH3 CH Br S0GGESTE1 ANS2ERS S0GGESTE 1 MARKS <m CH3 ) JBr < m for correct reagent and condition of each step." H2O <$<" m Correct steps <m < m for correct reagent and condition of each step." JCl <$<$<$<" m

CH3 )

JOH

CH3

CH OH

O0idise 2/propanol with hot acidified potassium dichromate. CH3 2; d" CH CH3 ) 5O6 CH3 CH CH3 )

OH O Heat </propanol with e0cess of concentrated sulphuric acid. CH3 CH2 CH2 OH CH3 CH CH2 ) H2O Reaction with h'drogen chloride at room temperature. CH3 C CH3 CH3 CH CH2 ) HCl Cl Heat 2/choloropropane with ethanolic potassium c'anide. CH3 C CH3 ) CH3 C CH3 ) JCN CN Cl Boiling 2 c'nopropane with dilute sulphuric acid. CH3 C CH3 CH3 ) ) 2 H2 O ) H CN C

CH3

COOH

NH$

EN1 O5 MARKING SCHEME