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AS/APR 2008/CHM301

UNIVERSITI TEKNOLOGI MARA FINAL EXAMINATION

COURSE COURSE CODE EXAMINATION TIME

: : : :

ORGANIC CHEMISTRY II CHM301 APRIL 2008 3 HOURS

INSTRUCTIONS TO CANDIDATES 1. This question paper consists of three (3) parts : PART A (10 Questions) PARTB (10 Questions) PART C ( 4 Questions) Answer ALL questions from all three (3) parts. i) ii) 3. Answer PART A in the Objective Answer Sheet. For PART B and PART C in the Answer Booklet. Start each answer on a new page.

2.

Do not bring any material into the examination room unless permission is given by the invigilator. Please check to make sure that this examination pack consists of: i) ii) iii) the Question Paper an Answer Booklet - provided by the Faculty/Branch Campus An Objective Answer Sheet - provided by Faculty/Branch Campus

4.

DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO

This examination paper consists of 12 printed pages
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PART A (20 MARKS) 1. Which of the following compounds undergoes dehydration to form only one compound without any isomer? A. B. C. D. CH3CH2CH(OH)CH3 CH3CH2CH2CH2OH (CH3)2C(OH)CH2CH3 CH3CH(CH3)CH(OH)CH3

2.

Which of the following will react with methanol under suitable conditions? I II III A. B. C. D. ethanoic anhydride ethanoyi chloride ethyl ethanoate I and II I and III II and III I, II and III

3.

Which of the following compounds CANNOT be prepared in one step from ethanoyi chloride? A. B. C. D. CH3COCH2CH3 CH3CONHCH3 CH3COOC3H7 CH3COOH

4.

The reaction that converts pentanol to pentanoic acid is called A. B. C. D. esterification reduction oxidation hydrolysis

5.

Which of the following compounds will produce a carboxylic acid on hydrolysis? I. II III A. B. C. D. CH3OH CH3CN CH3COCI I and II I and III Hand III I, II and II
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6.

Which of the following is FALSE regarding propyl butanoate? A. B. C. D. It can react with Grignard reagent to form an alcohol. It is soluble in water. It is formed by the reaction between propanol and butanoic acid. It can react with ammonia to produce an amide.

7.

Which of the following compounds will give a positive isocyanide test? A. B. C. D. Propanamide Propylamine Propanal Propanol

8.

Which of the following statements is TRUE concerning benzoyi chloride? I. II. III. A. B. C. D. It can react with ammonia to produce benzamide. It can be hydrolyzed to form benzoic acid. It can react with ethanol to form ethyl benzoate. II only I and II I and III I, II and III

9.

The compound with the highest pH when it is dissolved in water is A. B. C. D. CH3COCI CH3CH2OH CH3CH2NH2 (CH3CO)2O

10.

The reaction between benzaldehyde and an aqueous solution of sodium hydroxide is called A. B. C. D. Cannizzaro reaction iodoform reaction Aldol condensation oxidation

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PART B (40 MARKS)

QUESTION 1 Draw the structural formulae for the following compounds: a) b) c) d) trimethylamine phenylethanone 4 - methylbenzoyl chloride propyl butanoate (4 marks) QUESTION 2 Give the IUPAC names for the following compounds: a)

II II /-C-o-C-CH,

c)

d)

II |3 CH3 C - N - C H 2 C H 3 (4 marks)

CH-

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QUESTION 3 Draw the structures of the main organic product(s) formed in the following reactions: UAH, 4
-^

a)

CH2COOH

H2O

b)

CH 3 C O C CH 2 CH 3

c)

c ci

6H6

AICI, (4 marks)

QUESTION 4 Consider the following compounds: Compound A Compound B Compound C Compound D CH3CH2COOH CH3CH2CH2OH CH3CH2CH2NH2 CH3CH2COCI

Which of the above compound(s): a) b) c) has/have a fishy smell? will react with sodium to release hydrogen gas? will react with phenol to give an ester? (4 marks)

QUESTION 5 Write the balanced equations for the reaction between phenylamine, C6H5NH2 and the following reagents: a) b) CH3COCI excess CH3CI (4 marks)
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QUESTION 6 Compound X has with the following structure: CH3 CH3CH2_C-H OH a) b) c) What is the ILJPAC name for compound X? Give the class of compound X. Compound X will react with hot acidified potassium manganat(VII), KMnO4. i) ii) What is the name of the reaction? Give the structural formula for the organic product formed. (4 marks)

QUESTION 7 Draw the structures of the main organic product(s) formed in the following reactions:
ZnO A

a)

COOH

->- R
+

b)

CH3CH2CH2MgCI

co2

c)

CH3CHCICH3

NaOH(aq)

T
Sn cone HCI

d)

NO.

W (4 marks)

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QUESTION 8 Consider the following compounds: Compound V : Compound X : CH3COCH3 CH3CH2CHO CHO

Compound Y:

Compound Z : Identify the compound(s) that: a) b) c)

CH3CH2OH

will give yellow precipitate when heated with alkaline solution of iodine. will give a red precipitate when heated with Fehling solution. will release hydrogen chloride gas when treated with phosphorous trichloride. (4 marks)

QUESTION 9 Consider the reaction scheme below:

CH3COOH

Compound B H Compound A Step 1 SOCL

COOH
a) b) c) Name compound A.

Compound C

Draw the structural formulae for the compounds B and C. Give the reagents needed for Step 1 to occur. (4 marks)

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QUESTION 10 Consider the following compounds: Ethanamide Ethyl ethanoate Ethylamine Ethanoyl chloride a) Which compound(s) will react with nitrous acid to give i) ii) ethanoic acid? ethanol?

b)

Which compound(s) will dissolve in water to give i) ii) an acidic solution? a basic solution? (4 marks)

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PART C (40 MARKS)

QUESTION 1 The reaction scheme below shows the various reactions of compound S.
^ ,_ Compound T reagent 2 ^ f/ //

C o m p o u n dR ^

(^-

O c -OH

o H \\ II I \ ^ C - N -

^\s* ' ^ Compound W

\/ Compound U

Compounds

a)

Draw the structural formulae of compounds R, T and W. (3 marks)

b)

Identify reagent Z. (1 mark)

c)

Give the IUPAC name for the compound U. (1 mark)

d)

Compound S can be converted to alcohol H. i) ii) iii) Give the structural formula and IUPAC name for alcohol H. Write the balanced equation for the conversion of compound S to alcohol H. Name the reaction that has occurred. (5 marks)

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QUESTION 2

Compound X can be found naturally in certain food. O

II

HO-CH 2 CH 2 -C-CH 3 a)

Compound X

Name the functional group(s) present in compound X. (1 mark)

b)

Draw the structural formulae of the organic product formed when compound X is reacted with the following reagents: i) ii) iii) KCN LiAIH4 CH3COOH (3 marks)

c)

Suggest a chemical test to differentiate the following pair of compounds: i) ii) Compound X and its isomer Y, CH3CH(OH)COCH3. Compound X and its isomer Z, HOCH2CH2CH2CHO (6 marks)

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QUESTION 3 The reaction scheme below shows the various reaction of amide R. H CH3N CH3 Compound G CH3COCI Compound J Compound I Compound H O H H CH3 CH2NCH3 HCI

, - C - N ~CH3 Amide R

a)

Give the ILJPAC name of the following compounds: i) ii) amide R compound (2 marks)

b)

Draw the structural formulae for the following products: i) ii) iii) Compound I Compound J Compound H (3 marks)

c)

Give the reagents needed for: i) ii) Step 1 Step 2 (2 marks)

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d)

Compound S is an isomer of amide R and has the following structural formula: 0 H Compounds

CH3CH2-C-N - H

Give the formulae of the product(s) formed when compound S is heated with: i) ii) P2O5 NaOH(aq) (3 marks)

QUESTION 4 a) Draw the structural formulae of the organic products formed when propanal is reacted with: i) ii) iii) iv) lithium aluminum hydride acidified potassium dichromate 2,4,-dinitrophenyhydrazine excess CH3MgCI (4 marks) b) Propanal can also react with aqueous sodium hydroxide. i) ii) Draw the structural formulae for the product formed, Name the reaction that has occurred. (2 marks)

c)

With the help of a reaction scheme, show how the following compounds can be prepared from propanoic acid: i) ii) propanoic anhydride propene (4 marks)

END OF QUESTION PAPER

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