Alcohols Phenols and Ethers Flashcards
Alcohol
contains a -OH attached to a carbon chain
Phenol
contains a -OH attached to a benzene ring
Alcohol classification
number of alkyl groups attached to carbon bonded to a hydroxyl
- Primary (1º)
- Secondary (2º)
- Tertiary (3º)
Guide to Naming Alcohols
Step 1 Name longest chain with -OH group Step 2 Number longest chain closer to -OH group Step 3 Name substituents from -OH Step 4 Name a cyclic alcohol as cyclo
Thiols
organic compounds that contain a -SH group
Thiol Properties
have strong odors
- are used to detect gas leaks
- found in onions, oysters, and garlic
Ethers
contain an -O- between two carbon groups
Simple Ether Naming
named by listing the alkyl names in alphabetical order followed by ether
Anesthetics
inhibit pain signals to the brain such as ethyl ether
Cyclic Ether
contains an O atom in a carbon ring, is called a heterocyclic compound. Typically 5 - furan or 6 - pyran
Guide to naming ethers
Step 1
write the alkane name of the longer carbon chain
Step 2
Name the oxygen and smaller alkyl group as an alkoxy group
Step 3
Number the longer chain from the end nearer the alkoxy group and give its location
The boiling point of alcohols
contain a strongly electronegative O in the OH
- hydrogen bonding
- have higher boiling points than alkanes and ethers of similar mass
The boiling point of ethers
have an O atom, but no H is attached.
- no hydrogen bonding
- have boiling points similar to alkanes of similar mass
Solubility of alcohols and ethers in water
more soluble in water than alkanes because oxygen bond with hydrogen atoms in water
-alcohols with 1-4 Carbon atoms are soluble
Phenol
soluble in water and has an hydroxyl group that ionizes slightly.
Combustion
the reaction of an alcohol with O2 to produce CO2 and H2O
Dehydration of alcohol
occurs when heated with an acid catalyst and with the loss of an -H and -OH from the adjacent carbon atoms.
alcohol –> alkene
Sayteff’s Rule
the dehydration of secondary alcohol favors product with the smaller number of H atoms
Formation of Ethers
Ethers form when dehydration takes place at low temperature
Oxidation
process of increase in number of C-O bonds
loss of H
Reduction
process of decrease in number of C-O bones
increase of H
Oxidation-Reduction Map
Alkane -> 1 Alcohol -> Aldehyde -> Carboxylic Acid
2 Alcohol -> Ketone
Primary alcohol oxidized
one H is removed from -OH another -H is removed from the carbon bonded to -OH
aldehyde is produced
Secondary alcohol oxidized
one H is removed from -OH, another -H is removed from the carbon bonded to the -OH.
produces a ketone
one H is removed from -OH, another -H is removed from the carbon bonded to the -OH.
produces a ketone
Tertiary alcohol oxidized
do not readily oxidize, no room for O to bond to
Oxidation of ethanol in the body
ethanol is oxidized by enzymes in the liver.
aldehyde product impairs coordination
ethanol is oxidized by enzymes in the liver.
aldehyde product impairs coordination
Ethanol
acts as a depressant, kills more people than any other drug.
12-15mg/dL social drinker
30mg/dL by alcoholic
.4= coma/death
Oxidation of Thiols
An H atom is lost from two -SH groups, product is disulfide.
