Unit – IV

Stereochemistry, Reaction Mechanism and synthesis of drug

molecules
 Structural Representations of Organic Compounds
Newman projection Saw-HorseProjection Wedge
andDashRepresentation

Classification of Isomers

 Chiral compound : a compound that is optically active (achiral compound will

not rotate light). An object without symmetry isCHIRAL
 Optical activity - The ability of chiral substances to rotate
the plane of polarized light by a specific angle.

 Dextrorotatory - Ability of chiral substances to rotate the plane

of polarized light to the right.
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  Levorotatory - Ability of chiral substances to rotate the
plane of polarized light to the left.

 Conformational analysis of n-butane:

 Nucleophilic substitution reaction:

 Addition of HBr to propene.Markownikoff and anti Markownikoff’s

addition

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  Grignard additions on carbonyl compounds:

 Elimination reactions:

 Oxidation of alcohols using KMnO4

 Oxidation of alcohols using Chromic acid

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SHORT ANSWER QUESTIONS

1. Differentiate Enantiomers &diastereomers.

2. Mention the sequential rules applied in absolute configuration(R-S).
3. What conditions are present to determine whether a reaction will be Substitution or
elimination?
4. What is Markownikov’s rule? Justify the Markownikov’s addition of HBr to
isobutylene.
5. Using a Grignard reagent of your own choosing (not necessarily CH3CH2MgBr), how
would you make a sample of the alcohol 2-methylpropan-2-ol?
6. Why NaBH4 is less reactive than LiAlH4?
ESSAY ANSWER QUESTIONS

1. Discuss the Nucleophilic substitution reactions with primary, secondary & tertiary
alcohols.
2. Describe the synthesis and pharmaceutical applications of paracetamol.
3. Draw all conformations of n-butane and explain the conformational energy diagram for
n-butane.
4. Illustrate the hydride reduction mechanism of carbonyl compounds.
5. Explain the factors affecting SN2 mechanism.
6. “E2 reactions are stereospecific” Explain the statement.

OBJECTIVE ANSWER QUESTIONS

1) Which of the following groups has the highest priority according to the Cahn-Ingold-
Prelog sequence rules?
a) CH3 b) CH2Clc) CH2OHd) CHO
2) Which of thefollowing conformations of n-butane is the least stable ?
a) Gauche b) Anti c) Eclipsed d) fully eclipsed.
3) Stereoisomers that are exact mirror images of one another are called _____.
a) Diastereomers b)Enantiomers c) Constitutional isomers d)Geometrical isomers
4) The functional isomers of ethers are
a) Ketones b) Aldehydes c) Alcohols d)Esters.
5) Hexane and 3-methylpentane are examples of:
a. enantiomers.
b. stereoisomers.
c. diastereomers.
d. constitutional isomers.
e. 6) Which of thefollowing isomerisms is shown by alkenes but not by alkanes ?
f. a) conformational b)Optical c) Geometric d) Chain.
g. 7) An optically active compound should not posses ------------- [ ]

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 h. A) Plane of symmetry B) centre of symmetry C) alternate axis of symmetry D) all

8) An acceptor of pair of electron is termed as

a. nucleophile
b. electrophile

c. carbocation

d. anion

9) Which of the following statements regarding the E1 mechanism is wrong?

a. Reactions by the E1 mechanism are unimolecular in the rate-determining step.
b.  Reactions by the E1 mechanism are generally first order.
c.  Reactions by the E1 mechanism usually occur in one step.
d. Reactions by the E1 mechanism are multi-step reactions.

10) Which of the following alkyl halides would undergo SN2 reaction most rapidly?

a. CH3CH2-Br
b. CH3CH2- Cl
c. CH3CH2-I
d. CH3CH2-F
e. they react at the same rate
Fill in the blanks

1) N-acetyl-para-aminophenol is the chemical name of _________

2) The infinity of intermediate conformations are called __________
3) Conversion of an aldehyde to an alcohol is known as _________
4) The products of the reaction of a carboxylic acid and an alcohol would be_______
5) Molecules which are not superposable on their mirror images are called _________
6) ___________reaction at a saturated carbon is concerted.
7) Secondary alcohols on oxidation always produces __________
8) LiAlH4 and NaBH4 are both capable of __________ aldehydes and ketones to the
corresponding alcohol.
9) __________ & __________ are the precursors of aspirin.
10) ___________Rule implies that base-induced eliminations (E2) will lead
predominantly to the olefin in which the double bond is more highly substituted

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