SELF -ASSESSMENT EXERCISES

Chapters l-9

Explain the water solubility of alcohols.

2. Explain why tediary alcohols are stable to oxid a6e enzymest-/
3 Describo, using struclures, lhe mechanism of aclion of the dehydration of alcohots.
4. Draw the structures of phenol, cresol, resorcinol. hydrcqujnone.
,tt/ Are phenols acidic, basic or neutral ? Explain yo,.tr answer.

'v7.
Describe, using structures, the reactions of phenolwith melallic sodium, sodium hydroxide and sodium bicarbonale.
Describe, using structures, the oxidalisn of phenols.

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\^,hy is sait formation in phenots important ?
Why is an ether more water- soluble than its conesponding hydrocarbon ? -/r'/
10. Why are ethers very gcod solvents ?
11. VVhy is the boiling point of an ether similar to its conesponding hydrocaroon ?
12. Describe the i, yiro stability / stability of others.
Describe, using skLrc{ures, a cosmelic example which is based on the oxidation and reduction of thjol!.
14. \'rhat do thiols form when they react with bases ?
15. Describe, using structures, the similarity and differences belween carbonyl compounds and alkenes. What is the implication of
any difference behvegn the suuclures ?
16. Describe, using struclures, the water solubitity and boiling points of carbonyl compounds.
17. What is the difference in chemical reactivity between th€ aldehyde group and lhe ketone group ? \rvhy ?
18. Describe, using struclurcs, the oxidalion of aldehydes. How can aldehydes be protected against oxidatioi ?
aea Describe, using skuctures, some tests that are based on the oxidation of aldehydes, that are us6d to identiry aldehydes.
24. Oiscuss a clinica, use ofone of these aldehyde identiMng tests.
Descrlbe, usi:19 structures, the reduclion ot aldehydes.
Discuss an irnporlant biochemical oxJdation-reduction reaclion involving carbonyl cbmpoLhds, that js required to kee! the
body operating.
23 Describe, using structures, the rcduction of hydroquinones. How can lhis be prevenled ?
24 Describe, using skuctures, th6 hydralion of carbonyl compounds
25 Descibe, usinE staijctLrres, the mechanism of acetal formation from carbonyl cornpounds. Why is this reactioo impoMnt in
carbohydrates ?

26 Describe, using structures, lhe reaction oIa base with an aldehydes. What soecial conditjon ;s .equired for lhis .eaclion to
occur ?
Discr]ss the basicity of amines .

2E Discuss the water solubitity of amines.

Why do aromatic amioes differ significantly from alkyl amines in basicity ?

Describe the dealkylatlon and deamination reactions of amines.

31. \,/hy is the conjugation reaction important to amines ?
Describe, usang strudure$, the rcactions of an amine with an alkyl halide, an acid anhyd.ide, and a carbonyl compound.
33. What clinical signlficance does the oxidatjon ofsecondary amines to nitrosamines hav6 ?

Whal effect does dimer formation have on the boiling points ofcarboxyUc acids ?
Describe lhe water solubitity ofcarboxylic acids.
36. Compare the waler solubility of carborylic acids with its sotubility in atcohots.
37. De$cribe the resonanc6 slability ofthe carboxylate anion and its effect on the acidity ofcarboxylic acids.
3E. Describe, using struclures, the reactions of carborytic acids wilh metaltic sodiurn sodium hydroxide and soiijr,l ij;uatonate.
Discuss the reactivity ol carbox,vlic acids with b6ses.
40. Describe three methods of prepadng carboxylic acids.
41. Distinguish strL.turally between an alpha-keto acid and a beta"keto acid.
42. Describe, using structures, the mechanism of estermcation.
43. Describe the physical properties of ethers.
 l+3

44 Describe, using structures, the reaction ofesters wilh acids and bases.
45 What is an acid anhydride.
46 Discuss lhe baslcity ofamides.
47 How does resonance affecl the physical properties ol amides.
48. Compare the chemic.t stability ofthe amides to the esters.
49. Compare the physical propertjes of lhe esters, carbonates, carbamates and the ureas.
50. Oescribe, using structures, lhe rino opening aeactions of epoxides and lour membered ring heleroc,yc,es_
51. Define a het€rocycle.
Defrne a heteroatom.
Furan looks like an ether, but does not behave like one. Discuss.
54. Pyrrole behaves llke an aromatic compound. Discuss.
Both oxazole and isoxazole are aromatic compounds. Discuss.
56 Pyrazole and imidazole are aromatic compounds. Explain.
57. Puridjne, unlike its carbon analog benzene, is quite water soluble. Explain.
58 The benzopyroies behave like aromatic compounds. Explain.
DiscLrss the oxidation ofthe benzopyrroles.
60. Discuss the water sotubilily of lhe pur;nes.
61 What is a lactone,
42. Describe the acid/ base catalysed hydrolysis of a heterocycle containing a lactone.
63. Describe the jndole ring structute.
64. Describe the pl]ysico-chemical characleristics of the indote ring.
65. Defi ne a monosaccharide, disaccharide, oliogosaccharide.
66. Explain, using structures, the stereochemistry of D-gluGose and L-glucose.
67. Explain using structlJres what an anomedc carbon,an anome. and mutarotation. is.

yr' Describe, using structuaes, the glycosidic bonds in lactose and sucrose. Showwhich ofthe two ls a reducing sugar. Explain
your answer.
69 Describe, using struclures, the glyccsidic bonds in afiylose and giycogen. Explain how the linkages in giycogen facilitate the
release oI glucose molecules in the body.
70 What is the difference beiween a saponifable lipid and a non-saponifable Iipjd.
71 Describe the oxidalion of carbon - carbon double bonds in triacy,gycerols and its consequences. How can thjs oxidation be
prevented.
72. Explain the erfecl ofcas double bonds in fatty acids on their meltjng pojn!s.
73. Explain why it is necessary for the diet to contain linoteic acid and tinolenic acid.
74. Descaibe the primary, secondary and lertiary struclures ofproteins.
75. Explain, using structures, the stereochemistry of D-amino acid and L-amino acid,
76. Why are proline and glycine unusual amino acids ?
77. Define : zwatterion. amphoteric compound and isoeleclic point .

78. Define : ketogenic amino acids and glucogenic amino acids.

79. Describe, using structures, the peplide bond. Explain how its stnrcture affects its ptanarity.
80. \/vhat do the terms nStive conformation, native funclion and denaturation. mean ?
81. Discuss the factors that can prevent an alpha-hetix from foming.
82. Discuss the forces that hold a protein in a tertjary and quatefiary shape.