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TUTORIAL ANSWERS : INTRODUCTION TO ORGANIC CHEMISTRY (2012)

12. View Video: http://vimeo.com/13480728, Password: vjcchemistry

(i) What is the difference between a pair of tartaric acid enantiomers?
Answer:
They are non-superimposable mirror images of each other which rotate plane
polarized light in opposite directions.

(ii) Shown below is the structure of limonene:


(a) Draw the mirror image of limonene and indicate with * any chiral centres.
Answer:





nonsuperimposable mirror images

(b) There are 2 C=C bonds in limonene. Do they exhibit cis-trans isomerism? Why?
(View applet: http://www.vjc.moe.edu.sg/asknlearn/Chem/CisTransIsomerism.htm)

Answer:
Both C=C bonds cannot exhibit cis-trans isomerism.
The C=C bond in the ring is unable to form the trans isomer as the bond is limited by
ring strain.
The C=C in the side-chain cannot exhibit cis-trans isomerism as one C of C=C is
bonded to two identical H atoms.



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(c) (+)-limonene smells like lemon and (-)-limonene smells like orange. Do you think the
receptors in our nose which detect smell are chiral? Why?

Answer:
The receptors in our nose which detect smell are chiral because our nose can
differentiate between the two optical isomers.
The limonene isomers interact with the nose receptors in a lockandkey fashion. Hence,
only the correct fit will result in us smelling a particular scent.



13. Thalidomide was first administered as a racemate to combat morning sickness in pregnant
women in the 1960s which resulted in many birth deformations. What do you understand
by the term racemate.
(View video: http://vimeo.com/13480804, Password: vjcchemistry)

Answer:
Racemate is an equimolar mixture of a pair of enantiomers.








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SHAPES (FOR H2 ONLY)

REACTIVITY OF ORGANIC COMPOUNDS (FOR H2 ONLY)


17. Benzene is resonance stabilized due to the presence of delocalized pi electrons. Do you
expect the pi electrons in cyclohexa-1,4-diene to be delocalized.

Cyclohexa-1,4-diene


Answer :
No. This is because the double bonds in cyclohexa-1,4-diene are separated by two
single bonds. Benzene has alternating single and double bond which allows a
delocalization of pi electrons across all the adjacent aligned p orbitals.


INTEGRATED QUESTIONS (FOR H2 ONLY)

19. Acids are generally classified as inorganic or organic acids.

(a) Lactic acid, CH
3
CH(OH)CO
2
H, is a chemical compound that plays a role in several
biochemical processes. CH
2
(OH)CH(OH)CHO is a structural isomer of lactic acid.
Draw its displayed formula and explain why it is less acidic than lactic acid.


Answer








Anion of CH
3
CH(OH)CO
2
H is a carboxylate ion which is resonance stabilised.
CH
2
(OH)CH(OH)CHO is an alcohol and its anion is not resonance stabilised.


(b) The table below lists some properties of three samples of lactic acid prepared from
different natural sources.

sample source
effect on plane
polarised light
melting point /
o
C
A meat extract rotate clockwise 26
B fermentation of sucrose rotate anticlockwise 26
C sour milk no effect 18



C H
H
O
H
C
H
O
H
C
H
O
4




(i) With the aid of the structural formula of lactic acid, explain why samples A and B behave
differently towards planepolarised light.

Answer:
Samples A and B contain lactic acid but the lactic acid in B is the enantiomer/optical
isomer of the lactic acid in A. Hence, A and B behave differently towards plane
polarised light.









(ii) Explain why sample C has no effect on planepolarised light and suggest why it has a
different melting point from A.

Answer
Sample C is a racemic mixture of the two optical isomers of lactic acid. Hence, it does
not show optical activity.
Due to the mixture of isomers in C, the packing of lactic acid molecules in C is not as
regular as the packing of lactic acid molecules in A. Hence melting point in C is lower
than A.


(c) Maleic acid and fumaric acid are the two isomers of CH(CO
2
H)=CH(CO
2
H). The melting
points of maleic acid and fumaric acid are 131
o
C and 286
o
C respectively.

(i) Draw the two isomers.

Answer








(ii) Account in terms of bonding for the difference in their melting points.

Answer
Cis isomer has a lower melting point than trans isomer.
Cis isomer can form intramolecular hydrogen bonding leaving less sites available for
intermolecular hydrogen bonding.
Trans isomer forms intermolecular hydrogen bonding
CH
3
C
H
OH
CO
2
H
CH
3
C
H
OH
CO
2
H
C C
H
H
CO
2
H
trans
CO
2
H
C C
H H
CO
2
H
cis
CO
2
H