Chem 212
Quiz 2c
p.1
NAME__________________________________
Functional Groups and Alkanes (20 pts)
1. Underneath each structure, write the name for each of the following:
CH3
Br
CH3
H3C
H3C
CH3
H3C
2-bromo-5,6-dimethylnonane
cis-1,3-dimethylcyclopentane
When we learn stereochemistry,
this molecule may also be named
(1R,3S)-1,3-dimethylcyclopentane
2. Draw a line-bond structures for two different secondary amines with the formula C6H13N
[2(6) + 2 - 13 + 1]/2 = 1, so there must be one ring or one double bond. Because the N must be written explicitly,
the hydrogen attached to it must also be written explicitly. There are many possible answers.
H
NH
N
3. Draw a line-bond structures for two different carboxylic acids with the formula C5H8O2
[2(5) + 2 - 8]/2 = 2, and a carboxylic acid has one double bond, so there must be more unsaturation in the form of
one ring or one other double bond. There are many possible answers.
O
O
OH
OH
4. The reaction of chlorine (and light) with 3-methylpentane gives four organic products. Draw
the structure of the starting material and all of these products, and an arrow going from
starting material to product.
Cl
Cl 2, light
+
+
Cl
Cl
Cl
+
+
HCl
Chem 212
Quiz 2c
p.2
5. For each of the following pairs of structures, write whether they are identical, constitutional
isomers, cis-trans isomers, or different molecules.
8
H3C
6
CH 3CH 2CH 2CH(CH 3)CH 2CH(CH 3)CH 2CH 3
8 7 6 5
2 1
4 3
H3C
1
3,5-dimethyloctane
CH3
7
2
3
5
Identical
4
(Carbons numbered in both
for comparison)
CH3
CH3
CH3
Identical
Methylcyclopropane
CH3
CH3
cis/trans isomers
Cl
trans-1-chloro-3-ethylcyclohexane
After we cover stereochemistry,
another way to describe the
relationship between these is
"diastereomers", since they could
be called (1S,3S)- and (1R,3S)-
Cl
cis-1-chloro-3-ethylcyclohexane
6. Draw line bond structures for each of the following. Your answer must be in line-bond format
(e.g. like the structures above) to receive credit.
a. 2,3-dichlorodecane
Cl
Cl
b. trans-1,2-dimethylcyclobutane
CH3
CH3
c. 4-t-butyloctane