Chemistry

UNIVERSITI TUNKU ABDUL RAHMAN

|Faculty |: |Faculty of Engineering & Science | |Unit Code |: |UEMK1013 |
|Course |: |Chemical Engineering | |Unit Title |: |Chemistry for Engineering |
|Year/ Semester |: |Year 1/ Trimester 1 | |Lecturer |: |Dr. Loh Han Chern |
|Session |: |201101 | |Date |: |9th – 16th March 2010 |

Tutorial No. 2 [Part I: Multiple Choice Questions (each question carries 1 mark)].

Q1. Which is the IUPAC name for the following compound? [pic]

a) cis-1-isobutyl-3-methylcyclohexane b) cis-3-isobutyl-1-methylcyclohexane c) cis-1-butyl-3-methylcyclohexane d) trans-1-isobutyl-3-methylcyclohexane

Q2. What compound would yield an equimolar mixture of CH3CH2CH2CHO and CH3CHO upon treatment with O3, followed by Zn/HOAc?

a) 1-Hexene b) cis-2-Hexene c) trans-2-Hexene d) More than one of these

Q3. Select the structure of the major product formed in the following reaction.

[pic]

a) I b) II c) III d) IV

Q4. Which reagent or test could you use to distinguish between phenylacetylene and vinylbenzene?

a) NaOH/H2O b) Br2/CCl4 c) IR Spectroscopy d) CrO3/H2SO4

Q5. Which of the following statements about cyclooctatetraene is NOT true?

a) The compound rapidly decolorizes Br2/CCl4 solutions. b) The compound rapidly decolorizes aqueous solutions of KMnO4. c) The compound readily adds hydrogen. d) The compound is comparable to benzene in stability.

Q6. Which reagent(s) would serve as the basis for a simple chemical test that would distinguish between benzene and cyclohexene?

a) NaOH in H2O b) Br2 in CCl4 c) AgNO3 in C2H5OH d) NaHSO3 in H2O

Q7. The compounds shown below can be distinguished by which 1H-NMR characteristics?

[pic]

I) number of signals II) splitting III) integration IV) chemical shift

a) I, II, IV b) I, IV c) II d) IV

Q8. Identify the reagent(s) that would bring about the following reaction: CH3CH2CH2COCl ⎯⎯⎯→ CH3CH2CH2CHO

a) Li/liq.NH3 b) LiAlH[OC(CH3)3]3, ether c) NaBH4, CH3OH d) LiAlH4, ether

Q9. What is the major product of the following reaction? [pic]

a) I b) II c) III d) I and II in roughly equal amounts

Q10. Arrange the compounds in the order of increasing solubility in water (least soluble first). (help: add the lone pairs to the oxygen atoms and look for the possibility of hydrogen bonding between the molecules and water) [pic]

a) I, III, II, IV b) III, I, IV, II c) I, IV, II, III d) IV, I, III, II

Q11. List the following compounds in order of increasing level of oxidation: [pic] a) I, II, III b) III, II, I c) II, I, III d) III, I, II

Q12. The following transformation would be considered a(n)? [pic] a) reduction b) oxidation c) addition d) elimination

Q13. Prominent peaks in the IR spectrum are sufficient to distinguish between which compounds? I) butane and cyclobutane II) toluene and methylcyclohexane III) 2-pentanone and 3-pentanone IV) pentanal and 1-pentene

a) I, III b) II, III c) II, IV d) III, IV

Q14. Which of the molecules are primary alcohols?

[pic]

a) III, II b) IV, I c) II, III d) I, II

Q15. The major industrial process in use today for the production of methanol is the:

a) hydration of ethyne. b) hydrogenation of carbon dioxide. c) reduction of methanal. d) catalytic reduction of carbon monoxide.

Q16. Select the structure of the major product formed from the following reaction. [pic] a) I b) II c) III d) IV

Q17. Which is the proper name for the structure shown?

[pic] a) 2-Chloro-5-aldehydotoluene b) 6-Chloro-3-aldehydotoluene c) 2-Methyl-4-aldehydochlorobenzene d) 4-Chloro-3-methylbenzaldehyde

Q18. The reagent PCC in methylene chloride is successful in the selective oxidation of primary alcohols to aldehydes because:

a) PCC is a relatively weak oxidizing agent. b) primary alcohols cannot oxidize any further. c) hydration of the intermediate aldehyde is unable to take place in methylene chloride. d) methylene chloride is a reducing agent.

Q19. A compound with formula C5H10O gives two signals only, both singlets, in the 1H NMR spectrum. Which of these structures is a possible one for this compound?

a)

b)

c)

d)

Q20. Which compound is an acetal? [pic]

a) I b) II c) III d) IV

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