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Organic Tutorial 01

The document is a tutorial sheet for Organic Chemistry (CML101) at IIT Delhi for Semester 2, 2024-2025, containing various questions related to chiral centers, stereochemistry, reaction mechanisms, and product identification. It includes exercises on identifying chiral centers, assigning configurations, drawing structures in 3-D perspective, and analyzing reaction rates for SN1 and SN2 mechanisms. Additionally, it addresses specific reactions, symmetry elements, and the stereochemical relationships between different molecular structures.

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13 views3 pages

Organic Tutorial 01

The document is a tutorial sheet for Organic Chemistry (CML101) at IIT Delhi for Semester 2, 2024-2025, containing various questions related to chiral centers, stereochemistry, reaction mechanisms, and product identification. It includes exercises on identifying chiral centers, assigning configurations, drawing structures in 3-D perspective, and analyzing reaction rates for SN1 and SN2 mechanisms. Additionally, it addresses specific reactions, symmetry elements, and the stereochemical relationships between different molecular structures.

Uploaded by

dharneshjanga
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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department of chemistry, iit delhi

Semester 2 ; 2024-2025 ; CML101 : Organic Chemistry Tutorial Sheet 1


**********
Q1) The following structures represent molecules which may have two, one or no chiral centres. Indicate
which carbon atoms (if any) are chiral.
(i) CH3CHBrCH2OH (ii) HO2CHCClCO2H (iii) CH3(CH2)7CH(OH)-(CH2)7CO2H (iv) C2H5CH2COOCH3
(v) BrCH2CHD CH2Cl
Q2) Mark the identical, enantiomers & diastereomers (if any) in each part of the following set of compounds:

a)

b)
Q3) Assign the configurational symbol R or S to the compounds N, O, P and Q using the Cahn-Ingold-Prelog
system for the assignment of absolute configuration.

Q4) Draw, in the correct asymmetric (3-D) perspective, the following structures:
i) R-2-Hydroxy propanoic acid ii) R-2,3-Dibromo propanal.
iii) S-3-Methyl-3-methoxy-4-hexen-2-one iv) 3-R-4-S Dimethylhexane
Q5) Compound Y, C5H8O2, liberated CO2 on reaction with NaHCO3. It existed in two forms, neither of which
was optically active. Upon hydrogenation it yielded a compound of molecular formula C5H10O2, which could be
resolved into enantiomers. Suggest a structure for Y and write the reaction.
Q6) Compound Z, C6H8O2, liberated CO2 on reaction with NaHCO3 and was optically active. Upon
hydrogenation it yielded a compound of molecular formula C6H12O2, which was optically inactive. Suggest a
correct structure of Z and write the reaction.

Q7) Write the Sawhorse projection for A, shown below.


A CHO B CHO C CH2OH

H OH H OH HO H
HO H H OH HO H

CH2OH CH2OH CHO

Indicate the stereochemical relationship of A (shown above) with each of the two adjacent structures B & C.
What is the stereochemical relationship between structures B & C?
Q8) Draw the structures shown below as their corresponding Fischer projection formulae.

Q9) Identify the types and number of symmetry elements in each type present in the molecules A & B.
A B
Q10) Classify the following molecules as chiral or achiral.

Q11) Assign the absolute configurations of the following compounds.

2 2

2 3
2
3
2
Q12) In the following molecules, indicate the topicity of the hydrogen atoms marked H.

Q13) For the SN2 reaction,

3 2 2 3 2 2
Answer the following questions:
(a) What is the rate expression for the reaction?
(b) Draw an energy diagram for the reaction. Label all parts. You may assume that the products are of
lower energy than the starting reagents.
(c) What will be the effect on the rate of reaction if the concentration of n-propyl chloride is doubled?
(d) What will be the effect on the rate of reaction if the concentration of the NaOH is halved?
(e) How will the rate of the SN2 reaction change if the solvent is changed to 80% ethanol and 20%
water
Q14) For SN1 reaction,

Answer the following questions:


(a) What is the rate expression for the reaction
(b) Draw an energy diagram for the reaction. Label all parts. You may assume that the products are of
lower in energy than the starting reagents.
(c) What will be the effect on the reaction rate upon doubling the initial concentration of tbutyl chloride?
(d) Will the rate of the SN1 reaction change significantly if some water is added to the solvent ethanol.
Q15) Account for the following observations:
(a) Dehydrobromination of meso and racemic 1,2-dibromo-1,2-diphenylethane give cis and trans 1-
bromo-1,2-diphenylethene respectively.
(b) When the following deuterium labeled compound is subjected to dehydrohalogenation, under E2
condition, only one alkene product is formed. Identify the product and explain your answer.

CH3 H Br
D
H H

Q16) In the following reaction, explain the observation that the rate of substitution reaction of trans-isomer
is 70,000 while that of the cis-isomer is only 0.16.

SC6H5 SC6H5
C2H5OH

Cl OC2H5

II
Q17) Identify the major and minor products formed in the E2 elimination of the following compound. Explain
the reason behind the same.
Br

Q18) Identify the major products in the following reactions and explain your answer.

III

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