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F AlkanesAlkenesStereochemTutorial 3

This document provides a tutorial on alkanes, alkenes, and stereochemistry. It covers topics such as Newman projections of alkane conformations, assigning R/S configurations to chiral centers, drawing Fischer projections and examples of diastereomers, acid-catalyzed reactions of alcohols, mechanisms of rearrangement and addition reactions, predicting products of reactions involving halogenation, oxidation, elimination and substitution, and favoring SN1 vs SN2 mechanisms. It also defines protic and aprotic solvents and asks the reader to draw structures and predict major and minor products of reactions.

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Leong Yue Yan
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90 views4 pages

F AlkanesAlkenesStereochemTutorial 3

This document provides a tutorial on alkanes, alkenes, and stereochemistry. It covers topics such as Newman projections of alkane conformations, assigning R/S configurations to chiral centers, drawing Fischer projections and examples of diastereomers, acid-catalyzed reactions of alcohols, mechanisms of rearrangement and addition reactions, predicting products of reactions involving halogenation, oxidation, elimination and substitution, and favoring SN1 vs SN2 mechanisms. It also defines protic and aprotic solvents and asks the reader to draw structures and predict major and minor products of reactions.

Uploaded by

Leong Yue Yan
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as DOCX, PDF, TXT or read online on Scribd
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Alkanes, alkenes and stereochemistry

Tutorial

1. Consider 2-methylbutane. Sighting along the C2-C3 bond,


(a) Draw a Newman projection of the most stable conformation.
(b) Draw a Newman projection of the least stable conformation.
(c) If a CH3 <-> CH3 eclipsing interaction costs 11kJ/mol and a CH3 <-> CH3 gauche interaction
costs 3.8 kJ/mol, sketch a quantitative plot of energy versus rotation about the C2-C3
bond.

2. Assign R or S configuration to the chirality center(s) of the following molecules:

(a)
OH

C COOH

CH3
H

(b)

CH3

H C
COOH
HS

(c)

CHO

C
H OH
CH2OH

(d)

OH
H

Cl
H
3. Draw the Fischer projections of a pair of enantionmers, and the meso form of tartaric acid
(formula HOOCCH(OH)CH(OH)COOH). Give an example of a pair of diastereomers. Is a meso
compound optically active?

4. The acid-catalysed addition of water to the following alcohol yields two products. Giving the
mechanism of the reaction, explain why there is a major and a minor product.

5. The addition of hydrochloric acid to 1-isopropylcyclohexene yields a rearranged product.


Propose a mechanism for this.

Cl
+ HCl

6. Predict the products of the following reactions. Indicate the regiochemistry when applicable.

H2/Pd

Br2

OsO4

KMnO4
H3O+
7. Predict the products of the following reactions.

(a)
OH

HBr

ether

(b)

SOCl2

OH

(c)

Br
C2H5O-Na+
major and minor elimination products
EtOH

(d)

Cl
C2H5O-Na+
major and minor elimination products
EtOH

8. Using electron flow diagrams, describe the mechanisms of the E1, E2, SN1 and SN2 reactions
that may take place when chlorocyclohexane reacts with sodium hydroxide. For these
reactions, indicate which is the nucleophile, and which is the leaving group. Give the
conditions that favour each type of reaction.

9. List some of the most commonly used protic and aprotic solvents in organic chemistry. What
does “protic”mean?

10. (i) Draw the structure of (S)-2-bromobutane.


(ii) In order to convert it to (R)-2-butanol using a base such as OH-, would you choose a
reaction that favours the SN1 or SN2 mechanism? Explain.

(iii) In order to convert it to a racemic mixture of (R) and (S)- 2-butanol using a base such as
OH-, would you choose a reaction that favours the SN1 or SN2 mechanism? Explain.

11. Exposing ethylbenzene to chlorine under ultraviolet light yields two monochlorinated
compounds. Draw their structures, and indicate the major and minor products.

KKS 8/2017

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