Problem Set 1

Draw the structural isomers of the following compounds: Problem Set 3

1. Draw the structures of 13 chain and position isomers of an alkene with the formula C6H12.
1. 9 isomers with the formula C7H16
2. Name the compounds you drew.
2. 8 isomers of C9H20 with 5 carbons in the longest chain
3. Which compound/s will exhibit geometric isomerism?
3. 11 isomers of C9H20 with 7 carbons in the longest chain
4. Draw the structures of the intermediates and the major products of the following reactions:
4. Isomer of C13H28 with the shortest possible longest chain of carbons
Include stereoisomers, if any.
5. 12 cyclic compounds of C6H12
a. (CH3)2C=CCH2CH3 + HCl 
Name the compounds. b. 3,4-dimethyl3-heptene + HI 
c. 2-methylbutene + H+, H2O 
Using Newman projections, draw the most stable conformation of 2,2,4-trimethylpentane sighting
d. 3,5-diethyl-8-methyl-3-nonene + H+, H2O 
through C3-C4.
e. 2-methyl-2-butene + Br2 
Problem Set 2 f. Cis-2-butene + Br2 
g. Cyclopentene + Br2 
1. Predict the number of mono-chlorinated compounds from the reaction of each
C7H16 isomer with chlorine at high temperature.
Problem Set 4
2. Given 2,3-dimethylpentane, draw the structures of mono-chlorinated compounds
1. Draw the isomers of 6 alkynes with formula C6H10.
formed upon its reaction with chlorine in the presence of sunlight. Include 2. Name the compounds you drew.
stereoisomers, if any 3. Draw the I/TS and P. Include stereochemistry, if any.
3. Reactivity of halogens is as follows: F2 > Cl2 > Br2 > (I2). Chlorine is reactive and a. 1-pentyne + BH3  I/TS  P + H2O2, OH-  P
reacts with all free radical intermediates. Bromine, on the other hand, is selective b. 3-methyl-1,3-butadiene + HBr  I/TS ↔ I/TS  P
and reacts only with the most stable free radical intermediate. c. 1,3-cyclopentadiene + (1) O3 (2) Zn, HCl  P

a. Draw the structure/s of mono-brominated compound/s upon the reaction of d. 1,3-pentadiyne + (1) O3 (2) Zn, HCl  P

3-ethylpentane with bromine at high temperature. Include stereoisomers, if e. 2-butyne + H+, H2O  I/TS  P
f. Methylcyclohexene + KMnO4 (cold, alkaline)  P
any.
g. (R) 3-methyl-2-pentene + MCPBA  P + H2O  P
b. Give the mechanism of the reaction.
h. 2,5-dimethyl-3-hexyne + 1 mole HCl  I/TS  P
4. Among the 12 cyclic compounds of C6H12:
i. 2-pentyne + 1 mole Br2  I/TS  P
a. Which structures will exhibit geometric isomerism?
b. Which structures are chiral? Label the chiral carbons with *