Addu High School Hithadhoo, Addu

Write your name here Name Index Number Class

CHEMISTRY Monthly Test 01 (March, 2012) Advanced Level Unit 5: Benzene & Organic nitrogen compounds Section A

Total Marks

Answer ALL questions in this section. You should aim to spend no more than 10 minutes on this section. For each question, select on answer from A to D and put a cross in the box. . If you change your mind, put a line through the box and then mark your new answer with a cross . 1. Which statement about benzene is incorrect? A The empirical formula is C1H1 B The CC -bonding is delocalized. B The C6 ring is planar. D The reactivity reflects the presence of C=C bond (1) D 6 (1) (1)

2. How many signals do you expect to see in the 1H NMR spectrum of benzene? A 1 B 2 C 3

3. Which statement about the reaction of benzene with Cl2 in the presence of AlCl3 is incorrect? A The mechanism goes via an intermediate cation C The mechanism is electrophilic addition. B AlCl3 is a catalyst D The chlorobenzene is formed.

4. With which one of the following reagents does phenol react at 298 K and form a salt? A NaOH(aq) B Br2(aq) C Cl2 (aq) D HNO3(aq)

(1)

5. Which of the following is Secondary amine? A CH3CH2N(CH2CH3)2 B CH3CH2NH2 C CH3CH2NHCH2CH3 D C6H5NH2

(1)

6. Some recently developed polymers have unusual properties. (a) Which polymer is soluble in water? A. poly(propenamide) B. Poly(ethenol) C. Nylon -6,6 D. Kevlar (1)

Addu High School, Monthly Test 01 (March 2012)/ Chemistry (Grade 12)

1 of 4

(b) Which polymer has monomers with six carbon each ? (c) A. poly(propenamide) B. Poly(ethenol) C. Nylon -6,6 D. Kevlar

(1)

7. Formula of four organic compound A , B , C & D are shown below.

D (1) D

(a) Which compound reacts with dry solid PCl5 to form HCl gas A B C

(b) Which compound forms a green complex ion with CuSO4 (aq)? A B C D (1)

(c) Which compound forms a silver mirror with Tollens reagent A B C D (1)

Total for Section A = 10 Marks SECTION B Answer ALL the questions. Write your answers in the separate answer sheets provided. 8. This question is about the arene, benzene. The kekules structure of benzene can be shown as

(a) What is the molecular formula of benzene?

(1)

(b) The enthalpy change,H, for the addition of hydrogen to cyclohexene to form cyclohexane is120 kJ mol1.

(i) Calculate the enthalpy change of the hydrogenation reaction shown below.

(1)

Addu High School, Monthly Test 01 (March 2012)/ Chemistry (Grade 12)

2 of 4

(ii) Experimental work shows that H for the hydrogenation of benzene is actually 208 kJ mol1. What does this suggest about the stability and structure of benzene? (iii) Would you expect benzene to decolorise bromine solution? Justify your answer. 9. A reaction sequence is shown below. (3) (1)

(Total for question 11 = 6 Marks)

(a) In Step 1 benzene is nitrated to form nitrobenzene. (i) Give the reagents and conditions necessary for the reaction (ii) Name the mechanism for the reaction (iii) Give the mechanism for the nitration of benzene to form nitrobenzene Write an equation for the formation of the reactive inorganic species involved in the mechanism in Step 1. (b) (i) Name the type of the reaction taking place in Step 2 (ii) Suggest the reagent or combination of reagents for the second conversion (c) In step 3 benzanamine undergoes a substitution reaction to form compound A (i) Name the compound A formed in Step 3 (ii) Suggest the reagent or combination of reagents for the third (iii) The reaction in (c)(i) is carried out at a temperature maintained between 0C and 5C. Explain why this is so. Draw the structural formula of any other organic product formed if so (1) (2) (2) (1) (2) (2) (1) (3)

(d) Addition of a solution of compound A to an alkaline solution of phenol, gives a precipitate of the brightly coloured dye, 4-hydroxyazobenzene. Give the structural formula of 4-hydroxyazobenzene (2) (Total for question 12 = 16 Marks)

10. Kevlar is an organic polymer with five times the strength of steel. It is used in bullet-proof vests. A section of the Kevlar chain is shown below

(a) (i) Draw the structures of the two monomers which react to form the polymer. (ii) In this polymer formation two different molecules combine to form the polymer and water only Classify the type of polymerisation reaction which is occurring.
Addu High School, Monthly Test 01 (March 2012)/ Chemistry (Grade 12) 3 of 4

(2) (1)

(b) Another method of producing the same linkage is by ethanoylation, such as the conversion shown below.

State the reagent which could produce this conversion at room temperature and write an equation for the reaction. (2) (Total for question 1 = 5 Marks) 11. Aspartame is an artificial sweetener which is about 200-times sweeter than sucrose. It is a methyl ester of a dipeptide formed from the following two amino acids

(a) Draw the structure of a dipeptide formed between these two amino acids (b) (i) On the diagram of the structure of aspartic acid, identify, using an asterisk(*), a chiral centre in the molecule. (ii) Draw diagrams to show the two optical isomers of aspartic acid. (iii) State how the optical isomers of aspartic acid could be distinguished from each other. (c) (i) In solution, phenylalanine exists largely in zwitterion form. Give the Structural all but formula of the zwitterions form of phenylalanine. (ii) Use your answer to (i) to explain why phenylalanine has a high melting temperature.

(1)

(1) (2) (2)

(1) (2)

(d) Suggest the formula of the organic product formed when phenylalanine reacts, under suitable conditions, with (i) hydrogen ions, H+ (ii) hydroxide ions, OH (iii) ethanoyl chloride, CH3COCl (iv) methanol, CH3OH (1) (1) (1) (1) (Total for question 1 = 13 Marks) Total for Section B = 40 Marks
Addu High School, Monthly Test 01 (March 2012)/ Chemistry (Grade 12) 4 of 4