1 Squaric acid is an organic compound with the molecular formula C4H204 and is called 1 ,2-

dihydroxycycloutene-!,4-dion"
#a$ %he name shows that there are specific groups in the molecule" &raw the formulae of the
following groups that are in the molecule"
#i$ 'one
#ii$ 'ene
#iii$ cyclout Suggest a structural formula for squaric
acid" (2)
#d$ Suggest what you will oser*e when squaric acid reacts with
#i$ romine water
#ii$ 2,4-dinitrophenylhydra+ine reagent
#iii$ phosphorus pentachloride
2 %he production of petrol #gasoline$ has undergone industrialisation"
,n this process, coal powder is dissol*ed in hea*y oil" Compounds containing nitrogen and
sulphur are then separated at a high temperature" Hydrogen gas is passed through the mixture in
the presence of a catalyst" %he mixture will undergo distillation to produce light oil, moderate oil
and hea*y oil" %he light oil is used to produce petrol"
#a$ Suggest reasons why coal is used to
produce petrol" (2)
#$ Suggest one molecular formula for a type of hea*y molecule used in this process"
#c$ -xplain the existence of compounds containing nitrogen in fossil fuel li.e coal"
#d$ Suggest one reason why hydrogen is passed through the mixture"
#e$ State an appropriate catalyst for the hydrogenation process ao*e"
#f$ /i*e two ways to increase the octane numer and the performance of the
petrol" (2)
! 0 gaseous hydrocaron has the following composition y mass1 C, 23"456 H, 14"!5"
#a$ Calculate the empirical formula of this
hydrocaron" (2) 4 #a$ Saccharin is an artificial sweetener that is used in soft drin.s" ,t is
synthesised from methylen+ene as shown in the following diagram"
#$ 0"23 g of the hydrocaron from !#a$ has a *olume of 100 cm7 at standard temperature and
pressure" Calculate the relati*e molecular mass and write the molecular
formula for this hydrocaron" (2)
#i$ State the type of reactions represented y1
Step ,1
Step ,,1
#c$ &raw four structural formulae for this
hydrocaron" (4) Step ,,,1
#ii$ State the reagents used for1
Step ,,1
Step ,,,1
#$ 8hen methyl en+ene is nitrated with a mixture of concentrated nitric acid and sulphuric
acid, the product is two isomers with the molecular formula C,H,9:,"
#i$ &raw oth the isomers"
#d$ &raw two polymer repeating units that can e otained from the addition polymerisation
process of any of the
al.enes in #c$" (2)
#ii$ /i*e a rough outline for the mechanism
of this reaction" (4)
3 #a$ ;ased on the mass spectrum of the organic compound 0, it is disco*ered that the relati*e
molecular mass is 32" %he empirical formula for compound 0 is C,H2:"
#i$ 8hat is the molecular formula of compound 0<
= #a$ &raw the structural formula for
#i$ propenoic acid, C!H402
#ii$ !-phenylpropenoic acid
#ii$ Suggest fi*e possile structures for compound >" #&raw the structures$"
#$
#$ Suggest one experiment to differentiate
;ased on the molecule shown ao*e, answer the following questions"
#i$ &oes the molecule react with hydrochloric acid< ,f yes, write the molecular structure after the
reaction"
#ii$ ?ar. in that molecular structure, a
chiral caron atom" (!)
#c$ 0n ester with the molecular formula C3H,002 exists in wild plants" &raw the
ester isomers for this compound" (4)