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Answers to end-of-chapter questions

Chapter 30
1 a i 2-hydroxypropanoic acid ii OH
H C CH3

Examiners tip
[1]
Q1 part d i asks you for a mechanism you probably havent studied. Think logically and use what you know from other topics and from the question: 1 The reaction involves addition of 2H to a ketone the mechanism will be nucleophilic addition. 2 The question says that the first step involves nucleophilic attack on the carbon of the ketone group by an H ion. 3 The question says that there is water present.

 HOOC

[1]

Examiners tip
Q1 part a ii asks you to draw the other optical isomer of lactic acid. This is often done badly in exams. To help yourself to get it right, redraw the isomer of lactic acid shown here on the left-hand side of a sheet of paper, then put a vertical mirror line down the centre of the paper. Now draw the other isomer. Start with a C in the middle and a vertical bond to an OH this doesnt change. Then draw in the other three groups. In the first isomer they were (left to right) CH3, COOH, H. In the second isomer they will be H, COOH, CH3. The forward/backwards direction of their bonds doesnt change. The H is going backwards, the COOH is coming forwards, the CH3 is neither backwards nor forwards.

ii CH3COCOOH is planar and there is attack from hydride above and below plane of molecule; [1]  this gives equal amounts of the two optical isomers of CH3CH(OH)COOH. [1]  These cancel each other out, so there is no rotation of plane-polarised light. [1] Total = 19 2 step 1, preparation of 2-bromopropanoic acid CH3CH(OH)COOH + HBr CH3CHBrCOOH + H2O reagents used are: concentrated sulfuric acid and sodium (or potassium) bromide step 2, preparation of 2-aminopropanoic acid CH3CHBrCOOH + NH3 CH3CH(NH2)COOH + HBr reagents and conditions are: in ethanol (as solvent) heat in sealed tube (or under pressure)

[1 marks for reactants, 1 mark for products] [2]

iii It has a chiral carbon atom / four different groups bonded to same carbon atom. b i acidified potassium dichromate  heat/distil ii CH3CH(OH)COOH + [O] CH3COCOOH + H2O c i sodium borohydride and water  warm ii CH3COCOOH + 2[H] CH3CH(OH)COOH d i
H3C O H O H COOH H 3C OH C H

[1] [1] [1]

[1] [1]

[1 marks for reactants, 1 mark for products] [2]

 [1 marks for reactants, 1 mark for products] [2]

[1] [1]

[1] [1] [1] Total = 9

 [1 marks for reactants, 1 mark for products] [2]


+ C

COOH + H

H  dipoles  curly arrow from lone-pair electrons on hydride  curly arrow from C O to between O and H atoms (or to the O atom to form negative ion)  curly arrow from H O bond onto oxygen atom in water  products

[1] [1] [1] [1] [1]

3 a A chiral auxiliary is a group or molecule attached to the compound from which the chiral compound is formed. [1] The auxiliary ensures that during the chemical synthesis only one optical isomer can be made. [1] At the end of the synthesis the auxiliary molecule is removed. [1] b Use naturally occurring chiral molecules [1] that have a similar chirality to the compound required; [1] for example, sugars and amino acids. [1] Total = 6

AS and A Level Chemistry Cambridge University Press

Answers to end-of-chapter questions: Chapter 30

4 a

O N O


N H

O O  [1] b Thalidomide has two optical isomers: [1] one was toxic (caused fetal abnormalities); the other reduced morning sickness in pregnant women. Note, however, that the two isomers interconvert in the body, so that giving a pure dose of the non-toxic isomer will not prevent problems. [1] The toxicity was not checked; as a result, such checks are now compulsory. [1] Total = 4

b biodegradable polymers will not persist in the environment; [1] less litter; [1] no problems with disposal, e.g. burning/ landfill [1] c disposable packaging; [1] it is biodegradable [1] medical sutures and bandages; [1] the product of biodegradation is natural/ non-toxic [1] Total = 9

5 a i octane (C8H18)  C10H22 C8H18 + C2H4 ii cracking b i ethanol  C2H5OH C2H4 + H2O ii elimination/dehydration

[1] [2] [1] [1] [2] [1] Total = 8 [1] [1]

6 a A substance is biodegradable if it is broken down in the environment; by living organisms.

7 a any two of the following: increased risk of sunburn faster ageing of our skin skin cancer damage to our eyes, such as cataracts reduced resistance to some diseases. disrupt plant photosynthesis/disrupt food chains b Cl + O ClO or Cl + O3 ClO + O2 ClO + O3 2O2 + Cl overall reaction is O3 + O 2O2 or 2O3 3O2 Cl acts as a catalyst (it is regenerated)

[2] [1] [1] [1] [1] Total = 6

Answers to end-of-chapter questions: Chapter 30

AS and A Level Chemistry Cambridge University Press

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