ORGANIC CHEMISTRY TEST AS 1
NAME:_______________________________________________
1 The structure of glycolic acid is shown.
H O
H C C OH
OH
glycolic acid
(a) Complete the table to show what you would observe when an aqueous solution of glycolic acid
is added separately to each of the reagents. If a reaction occurs, state the functional group of
glycolic acid that is responsible for the reaction.
does a
reagent observation with glycolic acid reaction functional group
occur? /
Na2CO3(aq)
2,4-DNPH
acidified Cr2O72–
[4]
(b) Two reaction sequences to make glycolic acid are shown.
HCN and NaCN
sequence A HCHO X CH2(OH)CO2H
reaction 1 reaction 2
Br2
sequence B CH3CO2H CH2BrCO2H CH2(OH)CO2H
reaction 3 reaction 4
(i) Draw the structure of X.
[1]
2
(ii) Name the reagent for reaction 2.
....................................................................................................................................... [1]
(iii) Name the mechanism of reaction 3.
....................................................................................................................................... [1]
(iv) Suggest the essential condition for reaction 3.
....................................................................................................................................... [1]
(v) Reaction 4 occurs via an SN2 mechanism.
Complete the diagram for the mechanism for reaction 4.
Include all relevant charges, partial charges, curly arrows and lone pairs.
H O H O
H C C OH H C C OH
Br OH
–
OH
[2]
(c) Glycolic acid can also be made by reacting glyoxylic acid with NaBH4.
H O H O
NaBH4
C C H C C OH
O OH OH
glyoxylic acid glycolic acid
(i) State the role of NaBH4 in this reaction.
....................................................................................................................................... [1]
(ii) Write an equation for this reaction using molecular formulae.
Use [H] to represent NaBH4.
....................................................................................................................................... [2]
3
2 The diagram shows a reaction sequence starting from ethanal.
H
O OH
HCN and NaCN H2SO4(aq) H C
C P H3C C H C CO2H
reaction 1 reaction 2 reaction 3
H 3C H
CO2H H
ethanal
Q R
reaction 4
C
H 3C CO2H
(a) (i) Draw the displayed formula of P.
[1]
(ii) Name the type of chemical reaction that occurs in reaction 3.
....................................................................................................................................... [1]
(iii) Write an equation to represent reaction 4.
Use [O] to represent the oxidising agent.
....................................................................................................................................... [1]
(iv) State the reagents and conditions for reaction 4.
....................................................................................................................................... [1]
4
(b) Compound Q is formed as a mixture of two optical isomers.
(i) Explain what is meant by the term optical isomers.
.............................................................................................................................................
.............................................................................................................................................
....................................................................................................................................... [1]
(ii) Draw the two optical isomers of Q, showing clearly their three-dimensional structures.
[2]
(c) R can be used to make a polymer, W, in two steps.
addition intermediate NaOH(aq)
R polymer W
polymerisation
Draw one repeat unit of W.
[3]
5
(d) Compound Z, H2C=CHCH3, is produced from R.
Z can be used in a two-step process to produce 2-aminopropane.
(i) I n the first step, Z reacts with HBr to form two products. The structure of the product
depends on which intermediate is formed, intermediate I or intermediate II.
H H H
C
+ + C C CH3
H 3C CH3 H H
intermediate I intermediate II
Explain why intermediate I is more likely to form than intermediate II.
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
....................................................................................................................................... [2]
(ii) When intermediate I forms, the product of the first step is T.
omplete the diagram to show the mechanism for the conversion of Z to T.
C
Include all relevant charges, partial charges, curly arrows and lone pairs.
Z T
H
H H
H C +
C H 3C C CH3
C CH3
H3C CH3
H Br
H
Br
[3]
(iii) T can then be converted to 2-aminopropane.
T
H H
NH3
H 3C C CH3 H 3C C CH3
ethanol
Br NH2
2-aminopropane
Name the mechanism for this conversion.
....................................................................................................................................... [1]
6
(e) (i) Compound S, CH3COCO2H, can be reduced by LiAl H4.
omplete the equation using structural formulae to represent this reaction.
C
Use [H] to represent the reducing agent.
CH3COCO2H + ............................................................................................................ [2]
ther reducing agents containing Group 1 metal cations include LiBH4, NaBH4 and KBH4.
O
The strength of the reducing agent depends on the size of its cation.
(ii) Give the electronic configuration of the Na+ cation.
1s2 ................................................................................................................................. [1]
(iii) Suggest why ionic radius increases down Group 1.
.............................................................................................................................................
.............................................................................................................................................
....................................................................................................................................... [1]
[Total: 20]
7
Twopossiblemethodsofmakinglacticacidareshown.
O OH
reaction 1
C H3C C H
H 3C H reaction 2
CN
OH
H 3C C H
CO2H
OH O lactic acid
reaction 3 reaction 4
H 3C C H C
H3C CO2H
CH2OH
(ii) Statesuitablereagentsandconditionsforreactions1 and 3.
reaction reagents and conditions
[4]
(iii) Namethetypeofreactionthatoccursinreaction2.
.......................................................................................................................................[1]
(iv) Reaction 4 uses NaBH4.
IdentifytheroleofNaBH4 in this reaction.
.......................................................................................................................................[1]
(v) Lacticacidhasachiralcentre.
Statewhatismeantbythetermchiral centre.
.............................................................................................................................................
.............................................................................................................................................
.......................................................................................................................................[1]
[Total:18]
8
4 Cyclohexaneisacolourlessliquidusedinindustrytoproducesyntheticfibres.
Areactionschemeinvolvingcyclohexaneisshown.
Cl
reaction 1 reaction 2
(a) Reaction 1involvesafreeradicalsubstitutionmechanism.
(i) Statetheessentialconditionrequiredforreaction1 to occur.
.......................................................................................................................................[1]
(ii) Completethetabletogivedetailsofthemechanisminreaction1.
nameofstep reaction
................................. Cl 2 2Cl •
•
propagation + Cl • +
..............................
Cl
•
................................. + Cl 2 + Cl •
•
termination + Cl •
..............................
[4]
(b) Namethetypeofreactionthatoccursinreaction2.
..............................................................................................................................................[1]
