DEPARTMENT OF CHEMISTRY

CML101 (ORGANIC CHEMSITRY)

SEMESTER-I 2023-2024

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TUTORIAL 1

1. The concentration of a compound X dissolved in chloroform is 6.15 g per 100 mL of

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solution.
(a) A portion of this solution in a 5-cm polarimeter tube causes an observed rotation of
─1.2 o. Calculate the specific rotation of X.

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(b) Predict the observed rotation if the same solution were placed in a 10 cm
tube.
(c) Predict the observed rotation if 10 mL of the solution were diluted to 20 mL and

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placed in a 5 cm tube.

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2. The specific rotation [] of both (S)-2-butanol and (S)-2-pentanol are nearly identical
(+14º). If a 1M solution of (R)-2-butanol is mixed with an equal volume of a 1M solution
of racemic 2-pentanol,
The specific rotation of the resulting solution will be __________.

3. 4
The following structures represent molecules which may have two, one or no chiral
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centres. Indicate which carbon atoms (if any) are chiral.

(i) CH3CHBrCH2OH (ii) HO2CHCClCO2H

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(iii) CH3(CH2)7CH(OH)-(CH2)7CO2H (iv) C2H5CH2COOCH3

(v) BrCH2CHD CH2Cl
(vi)
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OH

Cl
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4. Mark the identical, enantiomers & diastereomers (if any) in each part of the following set
of compounds:
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(a)
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M
C
 (b)

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te
es
5. 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.

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Se
4
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6. Draw, in the correct asymmetric (3-D) perspective, the following structures:
i) R-2-Hydroxy propanoic acid
ii) R-2,3-Dibromo propanal.
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iii) S-3-Methyl-3-methoxy-4-hexen-2-one
iv) 3-R-4-S Dimethylhexane
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7. (a) 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
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molecular formula C5H10O2, which could be resolved into enantiomers. Suggest a structure for Y
and write the reaction.

(b) 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
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optically inactive. Suggest a correct structure of Z and write the reaction.

8. Write the sawhorse projection for

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\
CHO
H OH
M

HO H
CH2OH
C

Indicate the stereochemical relationship of the above compound with the below written two
structures.
CH2OH
CHO
H OH HO H
H OH HO H
CH2OH CHO
 9. Convert the following structure to corresponding Fischer projection formulae

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te
10. Identify the types and number of symmetry elements in each type present in the following
molecules (M and N).

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CH3 H
CH3 H CH3 CH3

m
H H CH3
H

H CH3 H
H

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CH3 CH3
M N

11. Classify the following molecules as chiral or achiral.

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12. Assign the absolute configurations of the following compounds.

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13. In the following molecules, indicate the topicity of the hydrogen atoms marked H.
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M
C
 14. For the SN2 reaction,

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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

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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?

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(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

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20% water

15. For SN1 reaction,

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(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
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are of lower in energy than the starting reagents.

(c) What will be the effect on the rate of the reaction on doubling the initial concentration of
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tert.butyl chloride
(d) Will the rate of the SN1 reaction change significantly if some water is added to the solvent
ethanol.
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16. 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.
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(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
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answer.
M

CH3 H Br
D
H
C

H
 17. 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.

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te
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18. Identify the major and minor products formed in the E2 elimination of the following
compound. Explain the reason behind the same.

m
Se
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19. Identify the major products in the following reactions and explain your answer.
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L1
M
C