Practice questions SCH212 Organic Chemistry

Stereochemistry and monofunctional groups(alkyl halides and alcohols)

Please answer all questions. If you have a problem with a

question consult your study guide or your lecture notes. All the
question have been covered in the study guide or lecture notes.

Question A.
Designate R or S configuration for each of the compounds.

Question B
Identify each of the following molecule as chiral or achiral.

Question C
1. Draw a dash-wedge structure for (3R)-3-methyl-5-hexen-3-ol

2. Draw a dash-wedge structure for (1R)-1-bromo-1,3,3trimethylcyclohexane

3. Draw all possible stereoisomers of 2,3-dichlorobutane and indicate

which ones are enantiomers.

4. Draw Fischer projection formulas for all stereoisomers of 2,4dibromohexane, giving stereochemical details for each structure

5. What is the complete IUPAC name of the following substance?

(Remember to give
stereochemical details, as relevant.)

Question D
Complete the following reactions

H3C
H

OH-

Cl

OH
H

H2SO4
Heat

H3C

Br

CH3

CH3

CH3OH

CH3CH2OH
Cl
Cl

Question E
1. State the type of reaction occurring in each of the following. If more
than one reaction type occurs label the major and minor product.
CH3
H3C

CH3

H 2O

Cl
CH3
H3C

CH3

H2SO4
Heat

OH
H
H3C

CH3

terButOH

Cl

H
H3C

CH3

CH3O-

Cl

2. Draw the complete mechanism of the E1 elimination of 2methylcyclohexanol using H3PO4 and heat.

3. The treatment of (S), 2-chlorobutane with H2O gives a racemic

mixture. With the help of a mechanism explain how the products
were synthesized and give name of each product.

4. Give a complete mechanism for the oxidation of CH3CH2OH using

Swern oxidation method and state one disadvantage of the reaction.