Name: _________________________________
Date ______________
Organic Chemistry
Alcohols, Ethers, and Thiols Practice
Part 1. Follow the directions to draw the molecule being described. Name the molecule you draw.
1.
Start with a 7 carbon chain.
Add 2 methyl groups at the 2nd and 4th carbon.
Add an alcohol group at the 2nd carbon.
Add an additional 4 carbon chain coming off the
6th carbon.
Name:
2. Start with a cyclohexane.
Add a methyl to one of the carbons.
Add a single oxygen to the carbon opposite the methyl.
Add a 2 carbon chain to that lone oxygen.
Name:
3. Start with a cyclohexane.
Add double bonds at the 1st, 3rd, and 5th carbons.
Add two methyl groups with 1 carbon separating them.
Add 1 bromine on the carbon that is in between
the two methyls.
Name:
4. Start with a cyclohexane.
Add double bonds at the 1st, 3rd, and 5th carbons.
Add an OH group somewhere on the ring.
Fill the empty carbons with iodines so that they are in
positions 2 and 4 on the ring.
Name:
Part 2: All of the following alcohol molecules have the same basic structure. The only thing that changes
each time is the placement of the –OH group. Name each molecule.
HO
HO
Name: ___________________________
Name: _______________________________
OH
Name: ____________________________
OH
Name: _______________________________
Part 3: Name the following ethers. Use –oxy if groups on either side of –O—are too complicated.
O
O
Name: ____________________________
Name: _______________________________
O
O
Name: ____________________________
Name: _______________________________
O
Name: ____________________________
O
Name: _______________________________
Part 4: Draw the following molecules. MOST are thiols and phenols.
Draw: 3-octanethiol
Draw: 2,3-diiodophenol
Draw: 1-ethoxy-2-butanethiol
Draw: 2-methylbenzenethiol
Draw: 1,2-dimethyl 3-chloro-5-propylphenol
Draw: 3-cyclobutylphenol
Part 5: Predict the products of the dehydration reaction below AND name them.
H
H
OH
H
H
H
C
C
C
C
C
H
H
H
CH3 H
H
+
Part 6: For each name listed below, there is a better and more correct name. Write the “more correct”
name on the indicated line.
Example:
5-methyl phenol
Should be: 1-methyl phenol

2,4,4-trimethyl-5-pentanol
Should be: ____________________

1,3,4-cyclohexatriol
Should be: ____________________

5-octanol
Should be: ____________________

methyl ethyl ether
Should be: ____________________

ethoxymethane
Should be: ____________________

3,5-dithioloctane
Should be: ____________________

2,5,6-trimethylphenol
Should be: ____________________
Part 7: Hydrogen bonding. Draw diagrams below illustrating how hydrogen bonding occurs between two
water molecules, two ethanol molecules and two methoxy methane molecules. One of the three diagrams
will not be able to show H-bonds. Label that diagram with “No H-bonds Possible”
H-bonding in water
H-bonding in ethanol
H-bonding in methoxy
methane
Part 8: Name the following organic molecules. They may be alkanes, alkenes, alkynes, alcohols, ethers,
thiols or phenols.
Name: ____________________
Name: ___________________
Name: __________________
Name: ____________________
Name: ___________________
Name: ___________________
Name: ____________________
Name: ____________________
Name: ___________________
Name: ____________________
Name: _____________________
Name: ___________________
Part 9: Draw the following.
Phenoxybenzene
2-cyclopropyl-3-heptanol
cyclopentoxyoctane