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LECTURE 11
Monday 2/8/17
CHAPTER 13
Alcohols, Phenols, and
Ethers
ALCOHOL REACTIONS (continued)
PROPERTIES OF ETHERS
• Much less polar than
• More soluble in water than __________
but less soluble than ___________
PROPERTIES OF ETHERS (continued)
• Hydrogen bonding of dimethyl ether: (a) with water and
(b) no hydrogen bonding in the pure state.
THIOLS: THE –SH (SULFHYDRYL) GROUP
• Most distinguishing characteristic
• ethanethiol –
• propanethiol –
• 1-propene-3-thiol and 3,3-di-(1-propenyl)disulfide –
• trans-2-butene-1-thiol, 3-methyl-1-butanethiol, and methyl1-(trans-2-butenyl)disulfide –
THIOL REACTIONS
• Oxidation forms disulfide (-S-S-) linkages, which are
important structural features of some proteins:
• Specific example:
THIOL REACTIONS (continued)
• Oxidation reactions can be reversed with a reducing agent
(H), such as H2, which regenerates the thiol:
THIOL REACTIONS (continued)
• Thiols react with heavy metals (Pb2+, Hg2+) to form insoluble
compounds, with adverse biological results:
POLYFUNCTIONAL COMPOUNDS
• Polyfunctional compounds are compounds with two or
more functional groups.
• Functional groups determine chemical properties of
compounds.
• Example:
POLYFUNCTIONAL COMPOUNDS (continued)
Chapter 14
ALDEHYDES AND KETONES
ALDEHYDES AND KETONES
• _____________________ have at least one hydrogen
attached to the carbonyl group.
• ________________ have two carbons attached to the
carbonyl group.
ALDEHYDES AND KETONES (continued)
• Examples:
NAMING ALDEHYDES
• Find the longest carbon chain that contains the aldehyde
group. (The carbonyl carbon is carbon number 1.)
• Change ending of the root hydrocarbon name by dropping –e
and adding –al.
• All other branches and groups are named and located using
standard IUPAC system.
• Examples:
COMMON ALDEHYDES
NAMING KETONES
• Find the longest chain that contains C=O.
• Using the root alkane name, drop the –e ending and change
to –one.
• Number the longest carbon chain so the C=O group has the
lowest number.
• Name and number other attached groups as before.
• Examples:
COMMON KETONES
PHYSICAL PROPERTIES
• The carbonyl group is moderately polar, but it doesn’t have
any hydrogen atoms bonded to the oxygen atom, so it cannot
hydrogen bond between molecules.
PHYSICAL PROPERTIES (continued)
• Because of the polarity of the C=O group, these groups can
interact, but the attraction is not as strong as hydrogen
bonding.
• This makes the boiling point of aldehydes and ketones
___________ than alkanes, but _________ than alcohols.
PHYSICAL PROPERTIES (continued)
PHYSICAL PROPERTIES (continued)
• The C=O group can hydrogen bond with water molecules
because the oxygen atom in the carbonyl group has a partial
negative charge that attracts the partial positive charge of a
hydrogen atom in the water molecule.
• This makes low molecular weight aldehydes and ketones
water soluble (they have small hydrophobic sections).
PHYSICAL PROPERTIES (continued)
ALDEHYDE AND KETONE REACTIONS
• Recall the oxidation of alcohols produces aldehydes and
ketones.
ALDEHYDE AND KETONE REACTIONS
(continued)
• The difference in reactivity toward oxidation is the chief
reason why aldehydes and ketones are classified in
separated families.
ALDEHYDE AND KETONE REACTIONS
(continued)
• The ease with which aldehydes are oxidized allows us to
test for the presence of aldehydes with
ALDEHYDE AND KETONE REACTIONS
(continued)
• In the presence of aldehydes
• In the presence of aldehydes
ALDEHYDE AND KETONE REACTIONS
(continued)