Topic 10 Organic Chemistry ANSWERS 10.

1
Functional Groups an !somerism S"#$"
1.Which of the following pairs represent members of an homologous series? ;
A. C2H4 and C2H6
B. C2HCl and C2H4Cl2
C. CH!"CH! and CH!CH2"H
#. C!H$C""H and C4H%C""H
%. Which names are correct for the following isomers of C
6
H
&4
?
2'meth(lpentane
2eth(l'2'meth(lpropane
2)!'dimeth(lbutane
A. * onl(
B. * and ** onl(
C. * and *** onl(
#. *)** and ***
!. Which compound is a member of the same homologous series as &'chloropropane?
A. &'chloropropene
B. &'chlorobutane
C. &'bromopropane
#. &)&'dichloropropane
4. Which formula represents an amide?
A. CH!CH2+H2
B. CH!CH2+,CH!-2
C. H2+CH2C"2H
#. CH!C"+H2
. Which of the following is an amine?
A. CH!CH2+H2
B. CH!C"+H2
C. '.CH2C"+HCH2C"/n
0
#. CH!CH2C 1 +
6. How man( different structural isomers ha2e the formula C4H%C&?
A. 2
B. !
C. 4
#.
$. How man( different isomers ha2e the formula C4H&3 ?
A. &
B. 2
C. !
#. 4
4.
%. 5he al6anes are a homologous series of saturated h(drocarbons.
,a- 7tate the meaning of each of the following terms.
,i- homologous series
[1]
,ii- saturated
[1]
,b- ,i- 7tate and e8plain the trend in the boiling points of the first fi2e al6anes.
[2]
,ii- 9i2e the structural formulas for the isomers of molecular formula C4 H&3 and state the
name of each one [2]
Ha2e a general formula
Contain onl( C'C single bonds
*ncreases *ncrease in mass leads to greater :an #e Waal forces
CH!CH2CH2CH! ; Butane
CH!CH,CH!-CH! ; 2'meth(l propane
&3. ,i- <ist three characteristics of an homologous series) and e8plain the term functional
group. [3]
,ii- #raw the &our structures of alcohols of formula C4H%"H. +ame each one and
label them as either primar() secondar( or tertiar( alcohols. [4]
(iii) Many organic compounds can exist as isomers. Draw and name an
isomer of ethanoic acid,
[2
]
9eneral formula=differ b( CH2 grp=gradual change in ph(s props=similar
chem. >rops ,an( 2-
?unc grp ; atom or grps of atom responsible for chem. >rops of
homologeous series ,reacti2e part of molecule-
CH!CH2CH2CH2"H ; butan'&'ol ; primar(
CH!CH,CH!-CH2"H ; 2'meth(l propan'&'ol ; primar(
CH!CH,"H-CH2CH! ; butan'2'ol ; secondar(
CH!C,CH!-,"H-CH! ; 2'meth(l propan'2'ol ; tertiar(
HC""CH! ; meth(l methanoate
Topic 10 Organic Chemistry 10.%
'hysical 'roperties o& Organic Compouns S"#$"
&. When the compounds below are listed in order o& ecreasing boiling point ,highest to lowest- what is the
correct order?
&. ethane
A. 4) !) &) 2
B. 4)!)2)&
C. !)4)&)2
#. 2) &) !) 4
2. fluoroethane !. ethanol
4. ethanoic acid
2. Which of the following is e8pected to be a gas at 2@ C?
!. Which compound is the most soluble in water?
A. Aethane
B >ropane
C. >ropan'&'ol
#. >entan'&'ol
4. 7tatement ,7-B 7olubilit( of alcohols in water decreases with increase in Ar.
C8planation ,C-B 5he relati2e proportion of the h(drocarbon part in alcohol increases with increasing Ar.
A. Both 7 and C are true.
B. Both 7 and C are false.
C. 7 is true but C is false.
#. 7 is false but C is true.
. C8plain wh( the boiling points of ethanol and ethanoic acid are considerabl( higher than the
boiling point of ethanal.
[3]
6. #iscuss the factors which affect the boiling points of co2alentl( bonded compounds b( reference to
the following pairs of organic substances) whose boiling points are gi2enB
D ethane ,&44 E- and butane ,2$! E-;
D ethane , &44 E- and bromoethane ,!&& E-;
D bromoethane ,!&& E- and ethanol ,!2 E-. [6]
Cthanol and ethanoic acid both contain H bonds
7ince H is attached to electroneg " atom.
Cthanal has onl( dipole forces due to C;"
9reater 2an de waals forces in butane
Caused b( larger Ar increases bp.
#ipole forces in bromobutane
#ue to polarit( of C'Br bondF.these are stronger than :an #e WaalsFhigher bp.
Cthanol contains H bonds
#ue to "'H bondF.these are stronger than dipoleFhigher bp.
Topic 10 Organic Chemistry 10.(
Reactions o& Al)anes an Al)enes S"#$"
&. Which statement is correct about the reaction between methane and chlorine?
A. *t in2ol2es heterol(tic fission and ions. ClG
B. *t in2ol2es heterol(tic fission and ClH radicals.
C. *t in2ol2es homol(tic fission and ions. ClG
#. *t in2ol2es homol(tic fission and Cl H radicals.
2. Which are characteristics t(pical of a free radical?
*. *t has a lone pair of electrons.
**. *t can be formed b( the homol(tic fission of a co2alent bond.
***. *t is uncharged.
A. * and ** onl(
B. * and *** onl(
C. ** and *** onl(
D. I, II and III
!. Which is the best description of the following reaction?
C2H4 I H2" J C2H"H
A. Addition
B. Condensation
C. #eh(dration
#. H(drogenation
4. Which chemical is most li6el( to be a starting material for a common pol(mer?
A. CH!CH2CH!
B. CH!CH2"H
C. CH!CHCH2
#.
. What will be formed when CH2 ; CH2 reacts with Br2 in the dar6?
A. CH2Br KCH2Br
B. CH!KCHBr2
C. CH2;CHBr I HBr
#. CHBr ; CHBr I H2
6. (a) Describe a chemical test to distinguish between alkanes and alkenes,
giing the result in each case. !"#
,b- +ame the t(pe of pol(meriLation reaction which C!H6 undergoes and draw the structure of a section
of the pol(mer chain formed from three monomer molecules.
[3]
$. 9i2e an eMuation for the complete combustion of methane) CH4. *dentif( t*o products formed b(
the incomplete combustion of methane and identif( one harmful effect caused b( one of the products.
[4]
4. 5he plastic >:C) pol(,chloroethene-) is made from the monomer chloroethene) C2H!C&) b( a
Bromine water
Al6anes ; sta(s orangeF.al6enes ; turns clear
Addition pol(meriLation
',CH,CH!-CH2 - '',CH,CH!-CH2 - '',CH,CH!-CH2 - ' ,2 mar6s-
CH4 I 2 "2 ; C"2 I 2 H2"
Carbon mono8ide ,poisonous=internal suffocation-
Carbon ,respirator( problems=asthma=bronchitis-
pol(meriLation reaction.
,i- #raw the structural formula of chloroethene. .&/
,ii- 7tate the t(pe of pol(meriLation reaction that occurs to ma6e pol(,chloroethene- and
identif( the structural feature needed in the monomer. .2/
,iii- #raw the structure of the repeating unit of pol( ,chloroethene-. .&/
,i2- C8plain wh( monomers are often gases or 2olatile liMuids) whereas pol(mers are solids. .2/
%. Al6anes are often described as ha2ing low reacti2it() although the( do react with halogens.
,i- C8plain wh( al6anes are unreacti2e. [2]
,ii- 5he first step in the reaction of propane with bromine can be represented b( the eMuation.
Br2J 2BrN
7tate the t(pe of species formed in this step and name the t(pe of bond fission. [2]
&3. Onder certain conditions ethene can be con2erted to ethanol.
,i- 9i2e a chemical test to identif( ethene and state what would be obser2ed.
,ii- 9i2e a balanced eMuation for the reaction to form ethanol from ethene.
,iii- 7tate the conditions necessar( for the reaction in ,ii-. [4]
CHCl ; CH2
Addition pol(mers
C;C ,unsaturated-
', CHClCH2 -'
Aonomers are small moleculesFlow ArFwea6 :an de waal forces..low bp
>ol(mers are 2 large moleculesFhigh ArFstronger :an #e Waals..high bp
+on polar
7trong C'C and C'H bonds
?ree radical
Hemol(tic fission
Bromine water
"range to clear
CH2 ; CH2 I H2" ; CH!CH2"H
Heat I ,almost conc- sulfuric acid ,as a catal(st-
Topic 10 Organic Chemistry 10.+
Reactions o& Alcohols S"#$"
&. Which compound is con2erted to butanal b( acidified potassium dichromate,:*- solution?
A. butan'&'ol
B. butan'2'ol
C. butanone
#. butanoic acid
2. What is the final product formed when ethanol) CH!CH2"H is reacted with acidified potassium dichromate,:*-?
A. ethanal
B. ethane
C. ethanoic acid
#. ethene
!. Which compound will undergo o8idation when treated with acidified potassium dichromate,:*-?
A. CH!CH2CH"
B. CH!C"CH!
C. CH!C""H
#. ,CH!-!C"H
4. ,a- >ropan'&'ol) in the presence of a small amount of o8idising agent) forms compound P)
and when reflu8ed with an e8cess of o8idising agent) forms compound Q.
,i- *dentif( a suitable o8idising agent and state the colour change. [2]
,ii- #raw the structural formulas of both compound P and compound Q. [2]
(b) $ome alcohols are oxidi%ed by heating with acidi&ed potassium
dichromate('I). If oxidation does occur, identify the possible oxidation
products formed by each of the alcohols below. Indicate if no oxidation occurs.
(utan)*)ol
(utan)")ol
")methylpropan)")ol
[
4]
. 5his Muestion is concerned with compounds ha2ing the molecular formula C!H4".
(a) #raw the full structural formulas of the three possible isomers and gi2e the name of each. [5]
(b) >redict how each of these isomers would beha2e when reacted with limited (i.e. not in
e8cess- acidified potassium dichromate,:*- solution and describe an( o,ser-ation that
could be made. Write the structures of an( organic products formed and gi2e their names. [6]
Cr2"$2' = HI "range to ,dirt(- green
P ; CH!CH2CH" Q ; CH!CH2C""H
Butanal and then butanoic acid
Butanone
+o o8idation ,tertiar( alcohol-
CH!CH2CH2"H ; propan'&'ol
CH!CH,"H-CH! ; >ropan'2'ol
CH!'"'CH2CH! ; metho8( ethane ,e8tension-
>ropan'&'ol ; propanal CH!CH2CH"
>ropan'2'ol ; propanone CH!C;"CH!
"bser2ations ;orange to dirt( green.
Aetho8( methane ; no reaction.
Topic 10 Organic Chemistry 10..
Reactions o& $alogenoal)anes S"#$"
&. 5he reaction between &'bromopropane and warm dilute sodium h(dro8ide solution is described as an
7+ 2 nucleophilic substitution reaction.
,i- C8plain each of the terms in 7+ 2. [3]
,ii- Write an eMuation and a mechanism for the reaction. [5]
2. ,i- &'bromopropane is described as a primary halogenoal6ane and 2'bromopropane is
described as a secondary halogenoal6ane. C8plain these terms with reference to the
two e8amples gi2en. [2]
,ii- 9i2e the structural formula of a tertiar( halogenoal6ane.
[1]
,iii- 7tate the t(pe of substitution reaction undergone b( tertiar( halogenoal6anes. [1]
!. 9i2e the structural formulas of the &our isomers of molecular formula C4H%Cl. 7tate the
name of each one and classif( it as primar() secondar() or tertiar(.
[]
,b- Cach of the isomers reacts with aMueous sodium h(dro8ide. 7tate what class of compound is
produced b( this reaction.
[1]
,c- ,i- *dentif( the t(pe of isomer ,primar() secondar( or tertiar(- which will react with
aMueous sodium h(dro8ide almost e8clusi2el( b( an 7+& mechanism. 7tate the
meaning of the s(mbols in the term 7+& mechanism.

[2]
7ubstitution) nucleophilic) second order
CH!CH2CH2Br I +a"H ; CH!CH2CH2"H I +aBr
>olarit( of C'Br bond curl( arrow from "H' nucleophile
Correct acti2ated comple8 formed Curl( arrow from Br' lea2ing group
>rimar( ; & carbon group attached to functional group
7econdar( ; two carbon groups attached to functional group
CH!C,CH!-2Br
7+&
CH!CH2CH2CH2Cl ; &'chlorobutane ; primar(
CH!CH,Cl-CH2CH! ; 2'chlorobutane ; secondar(
CH!CH,CH!-CH2Cl ; 2'meth(l &'chloropropane ; primar(
CH!C,CH!-2Cl ; 2'meth(l 2'chloropropane ; tertiar(
alcohols
5ertiar(
7ub) nucleophilic &st order reaction
Topic 10 Organic Chemistry 10./
Reaction 'ath*ays S"#$"
&. 5his Muestion refers to the compounds in the following reaction scheme.
C!H$Br
+a3H
C!H4"
38idation
C!H6"
38idation
C!H6"2
A 0 C 1
(a) 7tate a suitable reagent for the o8idation of 0 to C and C to 1. C8plain how the o8idation
of 0 to C could be achie2ed without further o8idation to 1. [3]
(b) 5he con2ersion of A to 0 ta6es place b( an 7+ 2 mechanism. 7tate what is meant b( the
term 7+2 and describe) b( using Rcurl( arrowsR to show the mo2ement of electron pairs) the
mechanism of this con2ersion.
[6]
2. 5his Muestion is about four compounds A) B) C and #) which can be made from ethene b(
the following reactions. All four compounds are liMuid at room temperature) and each
compoundSs molecular formula is shown.
C2H4 C2H" C2H4" C2H"2
! " # $
(a) Ose the information abo2e to identif( each of the compounds A2 02 C and 1 gi2ing the
name and structural formula of each one. []
(b) 7tate the t(pe of reaction occurring when A is con2erted to 0 and state the reagent reMuired.
[2]
,c- Compound A can react with bromine. Write an eMuation for this reaction and
name the product. 7tate a 2isible change which accompanies the reaction.
[3]
J
J
J
Acidified=HI potassium dichromate product must be distilled off before further o8idation
7ub) nucleophilic) 2
nd
order ,& mar6-
>olarit( of C'Br bond Curl( arrow showing C'Br bond brea6ing slowest step is first step
?orrnation of correct carbocation Curl( arrow showing attac6 of "H' on cation
A ; Cthene ; CH2CH2 B; Cthanol ; CH!CH2"H
C; Cthanal ; CH!CH2CH" # ; Cthanoic acid ; CH!CH2C""H
Addition reagent ; H2" ,and a sulfuric acid catal(st-
CH2CH2 I Br2 ; CH2BrCH2Br &)2'dibromoethane
"range to clear
Topic 10 Organic Chemistry 10.3
Nucleophillic Su,stitution $" ON"4
&. 5he al6aline h(drol(sis of primar( halogenoal6anes usuall( follows an 7+ 2 mechanism. ?or which
compound would the rate of h(drol(sis be fastest?
A. CH!CH2CH2?
B. CH!CH2CH2C&
C. CH!CH2CH2Br
#. CH!CH2CH2*
2. Which compound reacts most rapidl( b( a 7+& mechanism?
A. ,CH!-!CC&
B. CH!CH2CH2CH2Br
C. ,CH!-!CBr
#. CH!CH2CH2CH2C&
!. What is the maTor product when an halogenoal6ane is reacted with a large e8cess of
ammonia?
A. An amine
B. An amide
C. An amino acid
#. An al6ene
4. Which one of the chloroal6anes below will h(drol(se most rapidl(?
A. CH!CH2CH2CH2C&
. Which molecule does not act as a nucleophile in a reaction with a halogenoal6ane?
A. Cthane
B. Cthanol
C. Cth(lamine
#. Water
6. (i) Draw the structure of the four structural
isomers of +,-.+l.
[2
]
.
(ii) Identify one isomer in (iii) that undergoes a substitution reaction
mainly by an $/* mechanism.
[1
]
CH!CH2CH2CH2Cl CH!CH,Cl-CH2CH!
CH!CH,CH!-CH2Cl CH!C,CH!-,Cl-CH! tertiar(
5ertiar( one
(iii) 0rite the mechanism for the reaction that occurs when the isomer
identi&ed in (ii) is warmed with a1ueous sodium hydroxide. 2se curly
arrows to present the moement of electron pairs.
[3
]
$. ,a- ,i- #raw the structures of 2'chloropropanoic acid and 2'h(dro8(propanoic acid. [2]
,ii- 2'chloropropanoic acid can be con2erted to 2'h(dro8(propanoic acid b( nucleophilic
substitution. #efine the term nucleophile and state the nucleophile reMuired for this
reaction.
[2]
,b- #educe how the rate of reaction of CH2CH2CH2Br with +a"H would compare with that of the
compound CH2CH2CH2Cl with +a"H. C8plain (our answer b( referring to the #ata Boo6let.
.2]
>olarit( of C'Br bond Curl( arrow showing C'Br bond brea6ing slowest step is first step
?orrnation of correct carbocation Curl( arrow showing attac6 of "H' on cation
CH!CH,Cl-C""H CH!CH,"H-C""H
+ucleophile ; electron rich species=non bonded e pair=attracted to positi2e species
Warm dilute +a"H
Bromo is faster
#ata boo6let shows that strength of C'Br bond is wea6er ,since less polar- and so can be bro6en
more easil(.
Topic 10 Organic Chemistry 10.5
Conensation Reactions $" ON"4
&. What is the name of the compound CH
!
CH
2
CH
2
C""CH
!
?
A. But(l methanoate
B. Aeth(l butanoate
C. Aeth(l propanoate
#. >entanone
2.
?rom which t*o chemicals could this compound be s(nthesised?
A. butanoic acid and pentan'&'ol
B. butanoic acid and butan'&'ol
C. butanal and pentan'&'ol
#. pentanoic acid and butan'&'ol
!. CH
!
"H I CH
!
CH
2
C""H J CH
!
CH
2
C""CH
!
I H
2
"
5he forward reaction represented b( the eMuation abo2e is
A. addition.
B. esterification.
C. h(drol(sis.
#. neutralisation.
4. Consider the following reactionB
heat
CH
!
C""H I +H
!
J CH
!
C""+H
4
J CH
!
C"+H
2
What will be the final product if aminoethane ,eth(lamine- is used instead of +H
!
?
A. CH
!
C"+HCH
2
CH
!
B. CH
!
C"+HCH
!
C. CH
!
C"+H
2
#. CH
!
C"+H
2
CH
2
CH
!
. When ethanol is warmed with ethanoic acid in the presence of an acid catal(st a new
product is formed.
,a- Write the balanced eMuation for the reaction that ta6es place using the structural
formulas of the organic reactants and products. [3]
,b- 7tate how the organic product ma( be distinguished from the reactants and to which
homologous series it belongs.
[2]
,c- 7tate t*o reasons wh( concentrated sulfuric acid is used. [2]
,d- 7tate and e8plain how the solubilit( of the product in water compares with the
solubililt( of the two reactants in water. [2]
6. ,i- #raw the structural formula of meth(l methanoate. 7tate the conditions and the starting
materials for the preparation of meth(l methanoate in the laborator(. Write a balanced
chemical eMuation for the reaction.5]
,ii- #raw the structural formula of an isomer of meth(l methanoate. 7tate t*o ph(sical
properties and one chemical propert( that would be different for the two compounds.
7tate how each of these properties differ for the two compounds.
[5]
CH!CH2"H I CH!C""H CH!C""CH2CH! I H2"
& mar for products and reactantsF.& mar6 for eM sign
Cster has low bp=2olatileFhas strong smell.
As a catal(st shifts eM to UH7 ,as increase acidit( on <H7-
<ess soluble
Csters ha2e no H bonding
HC""CH!
materials ; methanol and methanoic acid
Conditions ; heat I acid ,sulfuric- catal(st
CH!"H I HC""H HC""CH! I H2"
*somer ; CH!C""H
>h(sical ; solubilit( in water=boiling point=2olatilit(
Csters cannot H bond but carbo8(lic acids can
Chemical ; Acidit(
Carbo8(lic acids will react with carbonates=metalsF.esters won t.
$. He8anedioic acid and &)6'diaminohe8ane react together to form a s(nthetic pol(mer.
5here are man( natural pol(mers) some of the most familiar being proteins formed from 2'
amino acids.
,i- 9i2e the structural formula of each monomer in the s(nthetic pol(mer.
[2]
,ii- 7tate the t(pe of pol(meriLation reaction that occurs between these two monomers
and identif( the structural feature needed in the monomers. [2]
,iii- #raw the structure of and state the t(pe of lin6age formed in this pol(mer) and
identif( the other product of this pol(meriLation reaction. [3]
3. (a) 4ien the structures of the repeating units of the polymers below,
identify the monomers from which they are formed.
[4]
', CH2'CH2 -'
', C"'CH,CH!- +H -'
', +H',CH2-6'C"'+H',CH2-4'C" -'
(b) Describe the essential di5erences between the structures of
monomers that form addition polymers and the structures of
monomers that form condensation polymers.
[2
]
+H2,CH!-6+H2 H""C ,CH!-4 C""H
Condensation pol(mer 2 functional groups per molecule
Amide lin6 ,'C;" V +H '- other product ; water
CH2;CH2
H""C'CH,CH!-'+H2
+H2,CH!-6+H2 and H""C ,CH!-4 C""H
,2 mar6s-
Addition ; C;C Condensation ; C;" group I nucleophile ,+H!)"H' C+' etc-
Topic 10 Organic Chemistry 10.6
Stereoisomerism $" ON"4
&. Which molecule possesses a chiral centre?
A. +H2CH2C""H
B. CH!CH,+H2-C""H
C. CH!C,+H2-2C""H
#. ,CH!-2C,+H2-C""H
2. Which compound is opticall( acti2e?
A. CH!C"CH,CH!-2
B. ,CH!-!CCH"
C. CH!CH2C"CH2CH!
#. CH!CH2CH,CH!-CH"
!. Which one of the following compounds is opticall( acti2e?
A. CH!CH2CH2CH2+H2
B. CH!CH2CHCH!
+H
C. CH!CH2+CH2CH!
H
#. CH!CH2+CH!
CH!
+. W has the structure
,i- 9i2e the structure of the geometrical isomer of W.
,ii- C8plain wh( W has a geometrical isomer.
,iii- #raw t*o structures for C$(C$%C$7Cl8C$() showing the relationship between them.
.2/
. 5here are geometrical isomers of the c(clic compound C4H6Cl2 #raw the structural
formula of two isomers and e8plain wh( these two isomers e8ist.
[3]
,b- ,i- #raw the structural formulas of t*o isomers of but'2'ene'&)4'dioic acid.
[2]
6. ,a- Consider the following compoundsB
&'chloropentane) 2'chloropentane) !'chloropentane
,i- *dentif( the compound which e8hibits optical isomerism and draw the structures of
the t*o isomers.
[3]
,ii- #escribe how these t*o isomers can be distinguished e8perimentall(.
[1]

CH! H
C;C
H CH2CH!
+o rotation of C;C bond
Airror images of enantiomers drawn in !#F,2 mar6s-
! # drawing of cis and trans c(clic isomers
Uestricted rotation in ring structures
drawing of cis and trans c(clic isomers
2'chloropentane
Airror images of enantiomers drawn in !#F,2 mar6s-
Uotation=effect on plane polariLed light.
$. ,a- #raw the structures of the two geometrical ,cis=trans- isomers of C4H4 ) gi2ing their
full names. .4/
,b- 5here are four isomers with the formula C H&3 which contain a three'membered carbon
ring. #raw these isomers and label them A) 0) C and 1.
[2]
,ii- *ndicate) b( writing two letters ,chosen from A) 0) C and 1- a pair of isomers that are
structural isomers and a pair that are geometrical isomers. .2/
%tructural isomersB
&eometrical isomersB
,iii- ?rom the four isomers A) 0) C and 1) draw the structure of an isomer that shows
optical isomerism and mar6 the chiral centre with an asteris6 ,H-. .&/
,c- Ose the e8amples from parts ,a- and ,b- to e8plain the e8istence of geometrical isomers. .&/
4. ,a- C8plain the term plane'polari(ed light and describe how the optical isomers of
C$(C$%C$ClC$( could be distinguished using a polarimeter.
.2/
,b- C8plain wh( a sample of C$(C$%C$ClC$( produced did not show optical acti2it(.
.&/
,c- 2'chloropropanoic acid and 2'h(dro8(propanoic acid can both show optical acti2it(.
*dentif( the feature which both molecules possess that accounts for this propert(.
When 2'h(dro8(propanoic acid is formed from 2'chloropropanoic acid) the product
shows no optical acti2it(. #educe the t(pe of nucleophilic substitution that ta6es place
and e8plain (our answer. .4/
drawing of cis and trans c(clic isomersF 2 mar6s
correctl( labeled as cis but'2'ene and trans but'2'ene
! # drawing of c(clic isomersF. 2 mar6s
Chain isomers 2 8 CH! on same CWs..or CH!CH2 ,2 mar6s-
Cis and trans isomers F2 8 CH! groups on different CWsF.,2 mar6s-
Cither of the geometric isomers
Uestricted rotation of a ring structure
<ight 2ibrating in one plane "ne isomer rotates it to left) other to right
Uacemic mi8ture
7+&
?ormation of carbocation intermediate is planar b( 7+& mechanism
+ucleophile can then attac6 with eMual chance on either side of cation.
CMual chance of both optical isomers being formed ; racemic mi8ture.
Topic 10 Organic Chemistry 10.10
Reaction 'ath*ays $" ON"4
&. 5his Muestion is about four compounds A2 02 C and 1. 02 C and 1 can be made from A b( the
following reactions. A2 0 and C are liMuid at room temperature) and each compoundSs molecular
formula is shown.
7odium was added to each liMuid compound. 9as bubbles formed slowl( in A but rapidl( in C.
(a) Ose the information abo2e to identif( each of the compounds A2 02 C and 1) gi2ing the
name an structural formula of each one. [4]
(b) ,i- 7tate the t(pe of reaction occurring when A is con2erted to 0 and C) and state a
suitable reagent and conditions for the reaction. [3]
,ii- C8plain wh( 0 is much harder to obtain than C in this reaction. [1]
(c) *dentif( the gas formed when A and C react with sodium and write an eMuation for the
reaction of C. +ame the other product of the reaction between sodium and C. [4]
,d- Arrange the compounds A) 0 and C in increasing order of boiling point ,lowest boiling point
first-. C8plain (our choice. [4]
,e- +one of the compounds A) 0) C and 1 e8ist as optical isomers. 7tate the structural feature
which is present in a compound that e8ists as optical isomers. #raw the structural formula of
the isomer of A that e8ists as optical isomers) [2]
a- A ; butanol ; CH!CH2CH2CH2"H
B; Butanal ; CH!CH2CH2CH"
C ; butanoic acid ; CH!CH2CH2C""H
# ; But'&'ene ; CH2;CHCH2CH!
b- i- o8idation E2Cr2"$ Acid and heat
ii- Hard to stop complete o8idationFneed to distil product B awa( from o8 agent.
c- H2 gas product ; sodium butanoate
2 +a ; 2 CH!CH2CH2C""H ; 2 CH!CH2CH2C""+a I H2 ,2 mar6s-
d- butanalF.butanolF.butanoic acid
butanol ; dipole ,wea6er intermolecular force-
Butanol ; H' bonds ,stronger intermolecular force-
Butanoic acid ; stronger H'bonds I dipole
e- as(mmetric carbon=4 different grps attached
CH!CH,"H-CH2CH!
2. Compound A is a bromoal6ane. When compound A reacts with warm
dilute sodium h(dro8ide solution an organic compound B is formed
which has a relati2e molar mass of $4.&2 and contains 64.4& X carbon)
&!.63 X h(drogen and 2&.% X o8(gen b( mass. Compound B can be
o8idised b( an acidified solution of potassium dichromate,:*- to gi2e
compound C which contains the same number of carbon atoms as
compound B.
,a- ,i- Calculate the empirical and molecular formula of compound B. [3 mar)]
,ii- 9i2e &our different possible structural formulas for isomers of
compound B which are consistent with the information that it has
been formed from the reaction of a bromoal6ane with +a"H ,aM-. [4 mar)s]
,iii- Which of the four isomers gi2en in ,ii- abo2e is not consistent
with the fact that compound B can be o8idised b( an acidified
solution of E2Cr2"$ to gi2e compound C? C8plain (our answer. [2 mar)s]
,i2- 9i2e the structures of the organic products which would be
formed when the remaining three structural isomers of compound
B are full( o8idised b( acidified E2Cr2"$. [3 mar)s]
,b- *t is shown that compound B e8hibits optical acti2it(.
,i- C8plain what is meant b( optical acti2it( and show clearl( the two
optical isomers of compound B. [4 mar)s]
,ii- 9i2e the structural formulas and names of compound A and
compound C. [4 mar)s]
,iii- +ame the mechanism which describes the reaction between
compound A and dilute sodium h(dro8ide solution. [1 mar)]
,i2- 9i2e the balanced eMuation for the reaction of compound B with
ethanoic acid in the presence of sulfuric acid and name the
functional group present in the organic product [3 mar)s]