Chapter 16. Answers to examination-style questions. Answers Marks Examiner s tips. 1 (a) (i) C 6 H 12 O 6 2C 2 H 5 OH + 2CO 2 (ii) fermentation

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1 Chapter 6 (a) (i) C 6 O 6 C 5 O + CO (ii) fermentation (b) (i) C 5 O + 3O CO + 3 O (ii) CO or carbon monoxide or C or carbon (a) (i) potassium (or sodium) dichromate(vi) or correct formula or potassium manganate(vii) (b) (i) SO 4 / Cl* / 3 PO 4 / NO 3 oxidation or redox C C=O (ii) Reagents can be: Tollens reagent or Fehling s/ Benedict s reagent or acidified potassium dichromate or ammoniacal silver nitrate or AgNO 3 + N 3 with propanone: stays colourless with Tollens reagent, stays blue with Fehling s/benedict s solution, stays orange with potassium dichromate in acid solution with propanal: there is a reaction. Depending on your reagent the following happens: Tollens reagent gives silver mirror Fehling s/benedict s reagent gives a red / brown / orange precipitate / solid acidified potassium dichromate goes green Learn the equation of fermentation and remember there is no oxygen there. The yeast respires anaerobically. If you give a contradiction of name and formula you lose the mark. Also if you give the name, you must give the correct name including the oxidation state. Acidified is accepted. *If you put KMnO 4 in the last part of the question you cannot have Cl here. The structure must clearly be an aldehyde showing the C=O AgNO 3 on its own will not score. Also potassium dichromate must show that it is acidified. If your reagent is correct then you can also have no change for the observation here for propanone. 3 (a) aqueous or solution in water or (aq) in the equation yeast or zymase Don t just say an enzyme. AQA AS Level Nelson Thornes Ltd 008

2 Chapter 6 anaerobic / absence of oxygen / absence of air or neutral p T in the range C only fermentation C 6 O 6 C O + CO C O + 3O CO + 3 O (b) dehydration is the elimination of water or removal of combined water from a compound / molecule catalyst = concentrated SO 4 or concentrated phosphoric acid or aluminium oxide C O C=C + O 4 (a) (i) compounds with the same molecular formula but different structural formulae / different structures (ii) C 3 6 O only (iii) C only (b) potassium dichromate(vi) / K Cr O 7 and acid / acidified / SO 4 / + remains orange or no change or no reaction orange to green (c) choice of reagents Learn these 4 points. You can use C 5 O but you should not use C 6 O. Don t say from a substance. You can use C 5 O but you should not use C 6 O. Also C C is not given credit. This is a definition so should be learnt. You can also have KMnO 4 / SO 4, but not Cl. Or remain purple if KMnO 4 used. Or goes from purple to colourless if KMnO 4 in acid used or gives brown precipitate or goes green if KMnO 4 neutral or in alkali. potassium dichromate(vi) / K Cr O 7 and acid / acidified / SO 4 / + or KMnO 4 / SO 4 Fehling s / Benedict s reagent Tollens reagent or AgNO 3 / N 3 or ammoniacal silver nitrate Not AgNO 3 alone. AQA AS Level Nelson Thornes Ltd 008

3 with the aldehyde C goes orange to green red solid silver mirror Chapter 6 goes purple to colourless / brown ppt. / green solution if KMnO 4 used red solid Potassium dichromate is more usual to do in school. with the ketone D remains orange or no change or no reaction or purple for KMnO 4 remains blue or no change or no reaction remains colourless or no change or no reaction These tests always come up, so learn the tests to distinguish aldehydes and ketones. If you can t learn them all pick one to really learn. (d) bromine alkane remains yellow / orange or no change or no reaction the alkene goes colourless or decolourised 5 (a) (i) C C C C O + [O] C C C CO + O (ii) C C C(O) + [O] C C CO + O (b) reagent: Fehling s/benedict s reagent or Tollens reagent or potassium dichromate conditions: if Fehling s/benedict s reagent boil, heat, warm if Tollen s reagent ammoniacal silver nitrate if potassium dichromate in acid This is the test for unsaturation. Don t say goes clear! If both observations are the same then you will get no credit for either. You can write C 4 9 C O but the product must show the aldehyde group CO, e.g. C 4 9 CO You could use C 3 7 C(O) but the product must show CO in the ketone, e.g. C 3 7 CO Aldehyde and ketone distinguishing tests again. with aldehyde product from (a)(i): if Fehling s/benedict s reagent used, get orange or brown or red precipitate if Tollens reagent used, get silver mirror if potassium dichromate used, solution goes green AQA AS Level Nelson Thornes Ltd 008 3

4 Chapter 6 with ketone product in (b)(ii): if Fehling s/benedict s reagent used, get no precipitate / no reaction if Tollens reagent used, get no silver mirror / no reaction if potassium dichromate used, get no reaction 6 (a) (i) C C C CO + [O] C C C COO (ii) pentanoic acid (b) (i) C C C C O or pentan ol (ii) primary Do not say nothing. int: In this case you can put C 4 9 CO going to C 4 9 COO You will be given credit for the abbreviation o or y 7 (a) % O =.6 % C O.6 6 If you do not calculate % O you cannot really carry on! ratio: 4 : 0 : ( C 4 0 O) (b) (i) type of alcohol: tertiary reason: no hydrogen atom on central carbon (ii) O C C C C O Isomer 3 Isomer 4 (c) (i) aldehyde (ii) C C C O + [O] C C CO + O (iii) name: butanoic acid structure: C C COO (d) advantage: fast reaction / pure product/ continuous process / cheap / high yield, 00% alcohol disadvantage: high technology / ethene from non-renewable source / expensive equipment 8 (a) C C C O C(O)C These are always the same method so you should always get them right. Always put in all the s. C 4 0 O is OK as a reactant but C 3 7 CO is not accepted for product. You cannot just have costly. (b) correct structures drawn for butanal, butanone and butanoic acid 3 You must show the CO, C=O and COO groups. AQA AS Level Nelson Thornes Ltd 008 4

5 Chapter 6 or the reaction of butan--ol with [O] to produce butanal and water balanced equation for the reaction of butan--ol with [O] to produce butanoic acid and water or balanced equation for the reaction of butanal with [O] to produce butanoic acid balanced equation for the reaction of butan--ol with [O] to produce butanone and water (c) correct structure drawn for -methylpropan- -ol name: -methylpropan--ol You must show the alcohol as O. If you put C O, then it looks like an aldehyde and will be marked wrong 9 (a) compounds with the same molecular formula but different structures due to different positions of the same functional group on the same carbon skeleton / chain (b) compound A is butan--ol only compound C is a ketone (c) (i) oxidation or redox (ii) K Cr O 7 or potassium dichromate(vi) acidified or SO 4 (iii) heat under reflux (iv) correctly drawn structure of -methylpropan--ol (v) correctly drawn structure of methanoic acid (d) (i) Tollens reagent or ammoniacal silver nitrate or Fehling s/benedict s reagent or acidified potassium dichromate(vi) (ii) correctly drawn structure of methylpropanal Another definition to learn! If you write the dichromate ion it will be marked wrong. A reagent must come out of a bottle. You must state the acid not just put + Use clearly drawn C C and C O bonds. You must have C O and C=O displayed. You must have C and C=O of aldehyde displayed.. AQA AS Level Nelson Thornes Ltd 008 5

6 Chapter 6 0 (a) (i) Isomer C C C O C O Name butan--ol -methylpropan--ol C C O (-)methylpropan--ol C C O butan--ol (b) (i) -methylpropan--ol (ii) dehydrating agent: conc. SO 4 or conc. 3 PO 4 or Al O 3 equation: C O C C + O C 4 9 O in equation is allowed provided RS is correct. (c) (i) isomer: butan--ol structure of the ketone: C ( ) C( ) O (ii) isomer: butan--ol or -methylpropan--ol structure of the aldehyde: either C C ( )C O or C( )C O AQA AS Level Nelson Thornes Ltd 008 6

7 Chapter 6 (iii) Choice of reagent again Reagent Tollens Fehling s (AgNO 3 /N 3 ) /Benedict s Observation stays colourless stays blue with ketone no change no change Observation silver mirror red solid with aldehyde black ppt orange / red brown / red ppt / solid (d) equation: C C C O + [O] C C COO + O name of product: butanoic acid (a) fermentation dehydration or elimination (b) (i) yeast / zymase (ii) concentrated sulfuric acid or phosphoric acid (c) (i) primary or (ii) sugar or glucose or ethanol is renewable or ethanol does not contain sulfurcontaining impurities or ethanol produces less pollution or is less smoky or less CO / C (d) C 6 C 4 + a fuel made from plants or organic matter C in the sugar plant initially so when fuel is burnt the same amount of C burns to give CO which is reabsorbed by sugar plants etc. ethanol produced in this way is a renewable resource, sugar this conserves valuable oil resources since the alternative method to produce alcohol is from ethane and steam You can put C 4 9 O here and C 3 7 COO This is not aqueous or dilute acid. This type of answer is really common sense. Nelson Thornes is responsible for the solution(s) given and they may not constitute the only possible solution(s). AQA AS Level Nelson Thornes Ltd 008 7

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