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Alcohols, Phenols, Ethers, Thiols Worksheet Key

1. Name the following compounds:
a)
CH3
CH3CH2CH2CH2CH2CH2CHOH

2-octanol

b)
CH3

CH3

2,4-Dimethyl-2 pentanol

CH

H3C
OH

C
H2

CH3

c)
CH3
HO
C
H2

H2 H2C
C
C
H2C

OH

H2
C

3,3-Diethyl-1,6-heptandiol

CH
C
H2

CH3

CH3

d)

CH2CH2OH

2-cyclohexylethanol

e)

OH
cis-1,2-cyclobutandiol

OH

2. Name the following compounds:

a)
H2
C

CH2

H2C

OH

CH

H2C

2,3-dimethylcyclooctanol

CH2
CH

CH

H3C

CH3

b)
O

Ethyl Methyl Ether

CH3

H3C

C
H2

c)

CH3

O CH3
CH CH3

2-methoxypropane

CH3
C O CH CH3
CH3 CH3

tert-butyl isopropyl ether

d)

CH3

e)
CH3
CH2

H2
C

C
H2C
H3C

f)

C
O

2-Ethoxy-3,3-dimethoxy-1-pentene
CH3

CH3

1-propanethiol

CH3CH2CH2SH
g)

SH
CH3CH2CHCH2CH3

3-pentanethiol

3. Complete the following reactions including all possible products. Name the family of
molecules that is formed:

OH
CH3CH2CHCHCH3
CH3

H OH
CH3CHCHCH2CH3

K2CrO4

O
CH3CH2CCHCH3
CH3

H2SO4 / H2O

H2SO4

O
H
O
2S
4
C
H
H
C
H
3C
3H

CH3CH CHCH2CH3

CH3
CH3CHOCHCH3
CH3

CH3CHCH2CH2CH CCH3
CH3
CH3
OH
CH3CHCH2CH2CHCHCH3
CH3
CH3

H2SO4

Major product

CH3CHCH2CH CHCHCH3
CH3
CH3

Minor product

K2CrO4
CH3CH2CH2OH

H2SO4 / H2O

O
CH3CH2CH

4. Complete the following reactions including all possible products. Name the family of
molecules that is formed:

CH3 O CH3

H2
C
H3C

+
SH

3 O2

2 CO2

3 H2O

H2
C
H3C

OH
CH3CH2CH2CCH2CH2CH3
CH3

SH

K2CrO4
H2SO4 / H2O

H3C

CH3

no reaction occurs under these

conditions

5. Draw several methanol (CH3OH) molecules, illustrating hydrogen bonding between

them.

CH3
H

H
H

H
H3C

CH3
CH3

O
H

O
CH3