UNIVERSITI MALAYA

UNIVERSITY OF MALAYA

PROGRAM ASASI SAINS

FOUNDATION STUDIES IN SCIENCE PROGRAMME

PUSAT ASASI SAINS

CENTRE FOR FOUNDATION STUDIES IN SCIENCE

SESI AKADEMIK 2018/2019 : SEMESTER 1

ACADEMIC SESSION 2018/2019 : SEMESTER 1

FAD 1006: KIMIA 2

CHEMISTRY 2

NOVEMBER 2018 MASA : 2 JAM

NOVEMBER 2018 TIME : 2 HOURS

ARAHAN KEPADA CALON:

INSTRUCTIONS TO CANDIDATES:

Kertas ini terbahagi kepada DUA BAHAGIAN.

This paper consists of TWO SECTIONS.

Jawab SEMUA soalan dalam BAHAGIAN A dan mana-mana EMPAT (4) soalan daripada
BAHAGIAN B. Soalan boleh dijawab dalam Bahasa Malaysia atau Bahasa Inggeris.
Answer ALL questions in SECTION A and FOUR (4) questions from SECTION B. Questions can
be answered in Malay or English.

Semua jawapan hendaklah ditulis pada kertas jawapan yang dibekalkan.

All answers must be written in the answer sheet provided.

(Kertas soalan ini mengandungi 16 soalan di dalam 11 halaman bercetak)

(This question paper consists of 16 questions on 11 printed pages)
 FAD 1006

BAHAGIAN A
SECTION A

1. (a) Sebutkan dua andaian mengenai kelakuan gas ideal.

(2 markah)

(b) Tulis ungkapan bagi nilai pembetulan dalam persamaan van der Waals bagi gas
sebenar.
(2 markah)

(a) State two assumptions regarding the ideal behavior of gases.

(2 marks)

(b) Write the expression for the corrected values in the van der Waals equation for
real gas.
(2 marks)

2. (a) Suatu sample Ar menduduki 5.0 L pada 25°C. Hitung perubahan isipadu Ar
sekiranya suhu ditingkatkan kepada 300°C. Tekanan adalah malar.
(2 markah)

(b) Suhu bagi 3.5 L gas yang asalnya pada STP telah ditingkatkan kepada 150°C
pada tekanan malar. Hitung tekanan akhir gas dalam atm.
(2 markah)

(a) A sample of Ar occupies 5.0 L at 25°C. Calculate the change in the volume of Ar
if the temperature is raised to 300°C. The temperature is kept constant.
(2 marks)
(b) The temperature of 3.5 L of a gas initially at STP is raised to 150°C at constant
volume. Calculate the final pressure of the gas in atm.
(2 marks)

3. (a) Senaraikan empat ciri-ciri fizikal sebatian organik.

(3 markah)

(b) Lakar formula struktur kembang dan struktur rangka bagi alkena termudah.
(1 markah)

(a) List four the physical properties of organic compounds.

(3 marks)
(b) Draw the expanded and skeletal structural formula for the simplest alkene.
(1 mark)

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4. (a) Takrifkan istilah-istilah berikut:

(i) Nukleofil
(ii) Radikal bebas
(2 markah)

(b) Nyatakan dua faktor yang perlu bagi molekul wujud sebagai isomer geometri.
(2 markah)
(a) Define the following terms:
(i) Nucleophile.
(ii) Free radical.
(2 marks)
(b) Give two factors for a molecule to exist as geometrical isomers.
(2 marks)

5. (a) Dengan menggunakan anak panah lekuk yang sesuai, tulis persamaan lengkap
dengan memberikan hasil bagi menunjukkan pembelahan ikatan untuk sebatian di
bawah:
(i) CH3CH2O—OCH2CH3
(ii) H3C—OH
(2 markah)
(b) Bagi setiap persamaan di bawah, tulis jenis tindak balas yang berlaku.
(i) H2C=CH2 + Cl2 → ClCH2CH2Cl
(ii) CH3CH2CHO + HCN → CH3CH2CH(OH)CN
(2 markah)

(a) With an appropriate curve arrow, write complete equations with the products
formed to show the bond fission for the following compounds:
(i) CH3CH2O—OCH2CH3
(ii) H3C—OH
(2 marks)
(b) In each of the following equations, write the type of reaction occured.
(i) H2C=CH2 + Cl2 → ClCH2CH2Cl
(ii) CH3CH2CHO + HCN → CH3CH2CH(OH)CN
(2 marks)

6. Beri nama sebatian berikut mengikut sistem penamaan IUPAC.

(i)

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(ii)

(iii)

(iv)

(4 markah)

Give the systematic IUPAC names for the following compounds.

(i)

(ii)

(iii)

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(iv)

(4 marks)

7. Ramal hasil yang diperolehi bagi setiap alkena berikut apabila ditindak balas dengan
hidrogen klorida.
(i) CH3CH=CHCH3
(ii) CH3CH=CHCH2CH3
(iii) (CH3)2C=CHCH2CH3
(iv) (CH3)2CHCH=CH2

(4 markah)

Predict the products formed when each of the following alkenes is reacted with hydrogen
chloride.
(i) CH3CH=CHCH3
(ii) CH3CH=CHCH2CH3
(iii) (CH3)2C=CHCH2CH3
(iv) (CH3)2CHCH=CH2
(4 marks)

8. Lengkapkan persamaan tindak balas berikut dengan memberi struktur dan nama hasil
organik yang didapati.

(i)

(ii)

(4 markah)

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Complete the following reaction equations by giving the structural formula and name the
organic products obtained.

(i)

(ii)

(4 marks)

9. Friedrich August Kekule telah mencadangkan struktur yang stabil bagi sebatian organik
benzena. Struktur tersebut menunjukkan penggiliran satu dan dua ikatan di dalam
hidrokarbon siklik. Bagaimanapun, terdapat kelemahan di dalam struktur ini.
(i) Terangkan kelemahan struktur benzena Kekule ini.
(ii) Nyatakan teori yang digunakan untuk memperbaiki struktur benzena Kekule ini.
(iii) Namakan satu sumber asli benzena.
(4 markah)

Friedrich August Kekule had proposed the structure of stable organic compound named
benzene. The structure features alternating single and double bonds in a cyclic
hydrocarbon. However, there are weaknesses in this structure.
(i) Explain about the weaknesses of Kekule benzene structure.
(ii) State the theory used to improve Kekule benzene structure.
(iii) Name a natural source of benzene.
(4 marks)

10. Tulis formula struktur untuk sebatian aromatik di bawah ini:

(i) 2,4,6-trinitroetilbenzena
(ii) 1,3-difenilpropana
(iii) 3,5-dinitroanalina
(iv) 2-fenilheptana
(4 markah)

Write structural formula for aromatic compounds below:

(i) 2,4,6-trinitroethylbenzene
(ii) 1,3-diphenylpropane
(iii) 3,5-dinitroanaline
(iv) 2-phenylheptane
(4 marks)

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BAHAGIAN B
SECTION B

11. (a) Satu sampel mengandungi 1.5 mol C6H6(g) di dalam bekas 20.0 L pada 30°C.
Hitung tekanan gas tersebut menggunakan
(i) persamaan gas ideal
(ii) persamaan van der Waals.
(R = 0.0821 L atm K-1 mol-1; a = 18.55 atm L2 mol-2; b = 0.119 L mol-1)
(5 markah)

(b) Tekanan separa bagi 10.0 L sampel gas campuran adalah 0.2 atm etana, 0.1 atm
metana dan 0.5 atm propana masing-masing pada 25°C. Hitung
(i) jumlah mol gas campuran tersebut.
(ii) pecahan mol metana.
(iii) jisim metana.
(R = 0.0821 L atm K-1 mol-1; RAM: H = 1, C = 12)
(5 markah)

(c) Kadar efusi bagi satu gas tepu yang tidak ketahui yang hanya mengandungi C dan
H didapati 1.154 kali lebih laju daripada Ar. Hitung jisim molar dan kenalpasti
gas yang tidak diketahui tersebut. (RAM: H = 1; C = 12; Ar = 40)
(3 markah)

(d) Hitung masa yang diambil bagi He untuk mengefusi sekiranya masa yang diambil
bagi oksigen untuk mengefusi dengan tekanan suhu dan isipadu yang sama adalah
45 saat. (JAR: He = 4; O = 16)
(2 markah)

(a) A sample containing 1.5 mol C6H6(g) occupies a 20.0 L vessel at 30°C. Calculate
the pressure of the gas using

(i) ideal gas equation.

(ii) van der Waals equation.
(R = 0.0821 L atm K-1 mol-1; a = 18.55 atm L2 mol-2; b = 0.119 L mol-1)
(5 marks)

(b) The partial pressures for a 10.0 L gaseous mixture are 0.2 atm ethane, 0.1 atm
methane and 0.5 atm propane respectively at 25°C. Calculate
(i) the total moles of the gas mixture.
(ii) the mole fraction of methane.
(iii) the mass of methane.
(R = 0.0821 L atm K-1 mol-1; RAM: H = 1, C = 12)
(5 marks)

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(c) The rate of effusion of an unknown saturated gas containing only C and H only
was found to be 1.154 times faster than Ar. Calculate the molar mass and identify
the unknown gas. (RAM: H = 1; C = 12; Ar = 40)
(3 marks)

(d) Calculate the time take for He to effuse if the time take for oxygen gas is 45
seconds for the same temperature, pressure and volume.
(RAM: He = 4; O = 16)
(2 marks)

12. (a) (i) Namakan ahli homolog alkana yang keenam, ketujuh dan kelapan.
(ii) Lakar formula struktur rangka bagi
(I) alkana ketujuh.
(II) alkohol ketujuh.
(iii) Lakar propana dan label karbon primer dan sekunder.
(7 markah)

(b) Tulis formula struktur untuk isomer yang mempunyai formula molekul, C6H12
yang menunjukkan
(i) isomer rantai
(ii) isomer kedudukan
(4 markah)
(c) Tulis formula struktur untuk empat isomer geometrik dengan formula molekul
C5H10
(4 markah)

(a) (i) Name the sixth, seventh and eighth members of the alkane homologous
series.
(ii) Draw the skeletal structural formula for the
(I) seventh alkane.
(II) seventh alcohol.
(iii) Draw propane and label the primary and secondary carbon.
(7 marks)

(b) Write structural formulae of isomers that has the molecular formula, C6H12
showing
(i) chain isomerism.
(ii) positional isomerism.
(4 marks)

(c) Write structural formulae of four geometrical isomers with molecular formula
C5H10
(4 marks)

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13. (a) (i) Susun alkana di bawah mengikut tertib takat didih yang semakin
meningkat. Jelaskan jawapan anda.

CH4, CH3CH3, CH3CH2CH3

(ii) Jelaskan perbezaan takat didih bagi sebatian berikut:

Alkana Takat didih / ºC

heksana 36.1
2 - metilbutana 27.8
2,2 - dimetilpropana 9.5

(iii) Adakah sebatian heksana larut di dalam air? Jelaskan jawapan anda.
(10 markah)
(b) Alkena P, Q dan R kesemuanya menghasilkan 2-metilbutana semasa
penghidrogenen dengan H2/Ni.
(i) Tentukan sebatian P, Q dan R.
(ii) Nyatakan alkena yang paling stabil di antara sebatian P, Q dan R.
Jelaskan.
(5 markah)

(a) (i) Arrange the following compounds in order of increasing boiling points.
Explain your answer.

CH4, CH3CH3, CH3CH2CH3

(ii) Explain the difference in the boiling points of the following compounds:

Alkane Boiling point / ºC

hexane 36.1
2 - methylbutane 27.8
2,2 - dimethylpropane 9.5

(iii) Will hexane dissolve in water? Explain your answer.

(10 marks)

(b) All P, Q and R alkenes produce 2-methylbutane upon hydrogenation with H2/Ni.
(i) Identify P,Q and R compounds.
(ii) State the most stable alkene amongst P, Q and R. Explain your answer.
(5 marks)

14. (a) Beri satu ujian kimia bagi membezakan sikloheksana dengan sikloheksena.
(5 markah)

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(b) Penghidratan 3 – metil – 2- pentanol, CH3CH2CH(CH3)CH(OH)CH3 akan

menghasilkan satu campuran alkena. Dengan bantuan persamaan tindak balas dan
mekanisma tindak balas, buktikan pernyataan tersebut. Berikan semua hasil
tindak balas dan label hasil utama.
(10 markah)

(a) Suggest a chemical test you would use to differentiate cyclohexane from
cyclohexene.
(5 marks)

(b) Dehydration of 3-methyl-2-pentanol, CH3CH2CH(CH3)CH(OH)CH3 yields a

mixture of alkenes. Validate the statement with the help of equations and reaction
mechanism. Write all products and label the major product.
(10 marks)

15. (a) Pengalkilan Friedel-Crafts merupakan tindak balas utama dalam sebatian
aromatik. Ianya merupakan tindak balas penukargantian.
(i) Terangkan secara ringkas apakah yang berlaku di dalam tindak balas
penukargantian ini.
(ii) Nyatakan jenis mangkin digunakan dalam tindak balas penukargantian ini
serta jelaskan fungsinya.
(iii) Beri dua sebab mengapa tindak balas penambahan tidak berlaku dalam
sebatian aromatik.
(5 markah)

(b) Kumpulan penukar ganti boleh dikategorikan sebagai kumpulan pengaktif,

kumpulan pendeaktif, pengarah orto-para dan pengarah meta.
(i) Apakah kesan kumpulan penukar ganti terhadap sebatian aromatik?
(ii) Nyatakan kesan kumpulan pengaktif dan kumpulan pendeaktif terhadap
sebatian aromatik tertukar ganti.
(iii) Apakah yang akan berlaku terhadap suatu elektrofil apabila pengarah orto-
para dan pengarah meta hadir dalam tindak balas?
(iv) Beri dua contoh pengarah orto-para dan dua contoh pengarah meta.
(10 markah)

(a) Friedel-Crafts alkylation is a main reaction in aromatic compounds. It is a

substitution reaction.
(i) Briefly describe what is happening in this substitution reaction.
(ii) State type of catalyst used in this substitution reaction and also its
function.
(iii) Give two reasons why addition reaction does not occur in aromatic
compound.
(5 marks)
(b) Substituent groups can be categorized as activating groups, deactivating groups,
ortho-para directors and meta directors.
(i) What are the effects of substituent groups toward aromatic compound?

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(ii) State the effects of activating and deactivating groups toward substituted
aromatic compounds.
(iii) What would happen to an electrophile when ortho-para directors and
meta directors exist in the reaction?
(iv) Give two examples of ortho-para directors and two examples of meta
directors.
(10 marks)

16. Bermula dengan benzena, dua sintesis berasingan telah dijalankan mengikut urutan
tindak balas A dan B.

Urutan tindak balas A : Pengalkilan → Pengoksidaan → Pembrominan

Urutan tindak balas B : Pengklorinan → Penitratan

Hasil akhir untuk urutan A merupakan sebatian meta manakala hasilan akhir urutan B
merupakan sebatian orto dan para.

Tulis persamaan tindak balas bagi A dan B ini dengan menulis struktur kimianya, bahan
uji dan keadaan tindak balas serta nama hasilan setiap proses mengikut aturan IUPAC
dalam semua tindak balas tersebut.
(15 markah)

Starting with benzene, two separate syntheses are carried out according to reaction
sequences A and B.

Reaction sequence A: Alkylation → Oxidation → Bromination

Reaction sequence B: Chlorination → Nitration

The final product for reaction sequence A is a meta product while the final products for
reaction sequence B are ortho and para products.

Write reaction equations for A and B including the chemical structures, reagents,
reaction conditions and also name each product according to IUPAC in all reactions.
(15 marks)

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