Course Instructor: Dr. Syed M.

Saad

INTRODUCTION TO ORGANIC CHEMISTRY

Practice Problems Set 5:

1. Rank the following alkenes in order of decreasing stability.

2. Following is the data of heat of hydrogenation of alkenes A, B, C, D, and E. Rank these alkenes in order of
increasing stability.

Alkene Heat of Hydrogenation; kJ/mol

A -221.5
B -210.0
C -250.6
D -345.2
E -195.5

3. Assign the cis/trans configuration to each of the following alkenes.

4. Assign the Z/E configuration to each of the following alkenes.

5. How many moles of oxygen gas will be required to completely ignite the following alkenes and alkynes?

i. 1 mol C40H80
ii. 2 mol C24H46
iii. 1 mol henicosatrict-50-ene
iv. 1 mol nonanonacont-9-yne

6. Draw the product(s) for the following ozonolysis reactions.

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 Course Instructor: Dr. Syed M. Saad

7. What starting material(s) is/are to be chosen for the synthesis of following aldehydes and ketones through
ozonolysis?

8. Draw the structure of products that are formed when 2-methylbut-1-ene reacts with each of the following reagents.

i. H2, Pt

ii. HBr

iii. H2O, catalytic H2SO4

iv. OsO4, then NaHSO3/H2O

v. Br2 in CCl4

vi. Br2 in H2O

vii. Br2 in EtOH

viii. O3, then Zn

ix. mCPBA in DCM

9. Draw the structure of products that are formed when hex-3-yne reacts with each of the following reagents.

i. One molar equivalent of Br2

ii. Two molar equivalents of Br2

iii. One molar equivalent of HBr

iv. Two molar equivalents of HBr

v. One molar equivalent of H2 and Lindlar catalyst

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 Course Instructor: Dr. Syed M. Saad

vi. H2(in excess)/Pt

10. Complete the following reactions by drawing the final products only.

11. Draw the chemical structure or write the IUPAC name, whatever asked, in the designated space provided.

Chemical Structure IUPAC Name

2,11-dimethyldodeca-2,6,10-trien-4,8-diyne

9-bromo-8-chloro-5-ethoxy-7-fluoro-10-iodo-6-
methoxy-4-nitroundeca-5,9-dien-2-yne