AQA Jun 2011 Paper 2 Q9 (with explained solutions) |

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AQA Jun 2011 Paper 2 Q9

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do not write outside the box a organic reaction mechanisms help chemists to understand how the reactions of organic compounds occur the following conversions illustrate a number of different types of reaction mechanism when bromopentane reacts with ethanolic koh two structurally isomeric alkenes are formed a i name and outline a mechanism for the conversion of bromopentane into pent ene as shown below ch ch ch chbrch ch ch ch chch ethanolic koh a ii draw the structure of the other structurally isomeric alkene produced when bromopentane reacts with ethanolic koh marks mark question continues on the next page turn over wmp jun chem do not write outside the box b name and outline a mechanism for the following conversion ch ch c ch br ch ch c ch br br marks wmp jun chem do not write outside the box c name and outline a mechanism for the following conversion ch ch ch br ch ch ch nh nh marks end of questions wmp jun chem

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mark s scheme genera qu uestion marking g guidance a i elimination l certificate of ed ucation a level c chemistry unit chemistry in a action june comments r m accept ba fix ase elimination b but no other nalise m if cova alent koh c of c br or nalise m for for orrect partial cha ore other partial nalise once only ne and two dots x any of mar ctant or wrong cept the correct u cept for the c h mal charge on c arges on c br charges he mechanism fo in any part of th or to show a bond hanism for wron rks for the mech n product if shown use of sticks fo or the molecule being attacked ng nalise c h cept correct stic cks mark for pref pen pen inco igno pen a lin max reac acc exc pen acc m must show an egatively charge ne m must show an bo ond towards the asonable attem re of f the appropriate m is independen aw ward full marks f orrect carbocatio co n b these are d arrow from the ed hydroxide ion arrow from a c appropriate c c pt has been mad e adjacent c h nt provided it is fr for an e mecha on ouble headed a arrows lone pair on the to a correct h a h bond adjacen c bond only aw de at the attack e oxygen of a atom nt to the c br ward if a on the h atom rom their origina anism in which m al molecule m is on the a ii st tructure for pen nt ene ch ch ch h ch ch b mark s scheme genera electrophilic c addition l certificate of ed ucation a level c chemistry unit chemistry in a action june r m both words s required for for m bon m way pen a lin max wro sho if h acc on the double br bond if wrong g m r the mechanism ignore partial ne egative charge o nd penalise partial y and penalise fo nalise once only ne and two dots x any of mar ong organic reac own or primary c br is used max cept the correct u l charges on br ormal charges he mechanism fo in any part of th or to show a bond rks for the mech hanism for rganic product i ctant or wrong or if carbocation x marks for the use of sticks eir mechanism arrow from the molecule e breaking of the cture of the tertia om arrow from the ed bromide ion to must show an m om of the br br at must show the m m is for the struc orrect carbon ato co m must show an ne egatively charge arbon atom ca n b these are d ouble headed a arrows double bond tow wards the br e br br bond ary carbocation w with br on the lone pair of elec owards the posit ctrons on the tively charged mark s scheme genera c m m nucleophilic c substitution l certificate of ed ucation a level c chemistry unit chemistry in a action june r m both words s required nalise m if nh nalise m for for tial charges e second mole o refore ignore an nalise once only nd x any of mar anic reactant or cept the correct u is negatively ch mal charge on c arged c or incorrect of ammonia is no y species here for a line and tw ot essential for m m wo dots to show rks for the mech r wrong organic use of sticks hanism for wron product if show ng n for pen pen part the ther pen bon max orga acc must show an m trogen atom of a nit m must show the bo ond to the br ato riginal molecule or m is for the struc condensed form a clo ose to the n ato m is for an arrow aw ward full marks f f the ammonia o of n b these are d arrow from the an ammonia mo e movement of a om m is indep lone pair of elec lecule to the c a a pair of electron pendent provide ctrons on the atom ns from the c br r d it is from their cture of the alkyl mula a positive c om w from the n h b for an sn mech n the intermedia ouble headed a ammonium ion charge must be which could be shown on or om m is the attack k bond to the n ato hanism in which ate carbocation arrows

Question 1 2 3 4 5 6 7 8 9

Topics to revise

AQA > Inorganic chemistry > Periodicity AS >

1 Periodicity

AQA > Physical chemistry > Equilibrium AS >

1 Dynamic equilibrium and factors affecting equilibrium

AQA > Organic Chemistry > Amines >

3 Reactions involving amines

AQA > Organic Chemistry > Alkenes AS >

3 Electrophilic addition

AQA > Organic Chemistry > Aromatic chemistry >

1 Structure and naming

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