1 Structure and naming

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Oxford Textbook Pages : 428 - 432

CGP Revision Guide Pages : 172 - 173

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Show Specification Ref : 3.3.10.1

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Question 1 / 5

January 2012 QP – Unit 2 AQA Chemistry A-level_question_10 consider the five cyclic compounds a b c d and e do not write outside the box cyclohexane cyclohexanol cyclohexanone oh br cyclohexene bromocyclohexane a the infrared spectra of compounds a b c and d are shown opposite write the correct letter a b c or d in the box next to each spectrum you may find it helpful to refer to table on the data sheet wmp jan chem do not write outside the box a i transmittance wavenumber cm mark a ii transmittance wavenumber cm mark a iii transmittance a iv transmittance wavenumber cm mark wavenumber cm question continues on the next page mark turn over wmp jan chem do not write outside the box b a simple chemical test can be used to distinguish between cyclohexane a and cyclohexene d give a reagent for this test and state what you would observe with each compound marks extra space c cyclohexanol b can be converted into cyclohexanone c give a reagent or combination of reagents that can be used for this reaction and state the type of reaction state the class of alcohols to which cyclohexanol belongs marks extra space wmp jan chem d cyclohexane a can be converted into bromocyclohexane e by a reaction that is similar to the reaction of methane either with chlorine or with bromine do not write outside the box name and outline a mechanism for the reaction of methane ch with bromine to form bromomethane ch br give one condition for this reaction to occur write an equation for each step in your mechanism marks extra space end of questions wmp jan chem
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Question 2 / 5

June 2011 QP – Unit 2 AQA Chemistry A-level_question_9 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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Question 3 / 5

June 2011 QP – Unit 4 AQA Chemistry A-level_question_8 do not write outside the box the hydrocarbons benzene and cyclohexene are both unsaturated compounds benzene normally undergoes substitution reactions but cyclohexene normally undergoes addition reactions a the molecule cyclohexatriene does not exist and is described as hypothetical use the following data to state and explain the stability of benzene compared with the hypothetical cyclohexatriene h h h kj mol h kj mol marks extra space question continues on the next page turn over wmp jun chem do not write outside the box b benzene can be converted into amine u by the two step synthesis shown below reaction no reaction nh the mechanism of reaction involves attack by an electrophile give the reagents used to produce the electrophile needed in reaction write an equation showing the formation of this electrophile outline a mechanism for the reaction of this electrophile with benzene marks extra space wmp jun chem c cyclohexene can be converted into amine w by the two step synthesis shown below do not write outside the box reaction compound reaction nh suggest an identity for compound v for reaction give the reagent used and name the mechanism for reaction give the reagent and condition used and name the mechanism equations and mechanisms with curly arrows are not required marks extra space question continues on the next page turn over wmp jun chem d explain why amine u is a weaker base than amine w do not write outside the box marks extra space end of questions acknowledgement of copyright holders and publishers question extracts from www ecpi org copyright aqa and its licensors all rights reserved wmp jun chem
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Question 4 / 5

June 2015 QP – Unit 4 AQA Chemistry A-level_question_8 do not write outside the box equations for the hydrogenation of cyclohexene and of benzene together with the enthalpies of hydrogenation are shown h h h kj mol h kj mol a i use these data to show that benzene is kj mol more stable than the hypothetical compound cyclohexa triene mark a ii state in terms of its bonding why benzene is more stable than cyclohexa triene mark b three carbon carbon bonds are labelled on the structures shown these bonds are of different lengths write the letters w x and y in order of increasing bond length mark wmp jun chem c the structures of two cyclic dienes are shown do not write outside the box cyclohexa diene cyclohexa diene c i use the enthalpy of hydrogenation data given opposite to calculate a value for the enthalpy of hydrogenation of cyclohexa diene mark c ii predict a value for the enthalpy of hydrogenation of cyclohexa diene mark c iii explain your answers to questions c i and c ii in terms of the bonding in these two dienes marks turn over wmp jun chem
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Question 5 / 5

June 2016 QP – Unit 4 AQA Chemistry A-level_question_4 do not write outside the box compound x clch cocl is used as a reagent in organic synthesis a the mass spectrum of x contains several molecular ion peaks a i chlorine exists as the isotopes cl and cl in a ratio calculate the m z value of the most abundant molecular ion peak in the mass spectrum of x mark a ii the most abundant fragment ion in the mass spectrum of x has m z draw the displayed formula of this fragment ion mark a iii a molecular ion of x that contains one cl atom and one cl atom undergoes fragmentation to form an ion with m z and one other species write an equation for this fragmentation show which isotope of chlorine is present in each product species marks b one important reaction of x is in the preparation of compound p as shown alcl cl ch c cl ch cl hcl wmp jun chem b i draw the structure of the electrophile formed by the reaction of x with alcl do not write outside the box mark b ii outline the mechanism for the reaction of the electrophile from part b i with benzene in the preparation of p marks c compound q is an alternative product that could be formed when x reacts with benzene cl ch describe how you could distinguish between p and q by a test tube reaction give the reagent used and the observation with each compound marks reagent observation with p observation with q turn over wmp jun chem do not write outside the box d x is also used to make the compound hoch cooh this compound is polymerised to form the polymer known as pga pga is used in surgical sutures stitches d i draw the repeating unit of pga mark d ii production of pga occurs via a cyclic compound two hoch cooh molecules react together to form the cyclic compound and two molecules of water draw the structure of this cyclic compound mark e poly propene is also used in surgical sutures e i draw the repeating unit of poly propene mark wmp jun chem do not write outside the box e ii suggest an advantage of surgical sutures made from pga rather than from poly propene explain your answer marks turn over for the next question turn over wmp jun chem
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