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Some Compounds with Oxygen, Sulfur, or Halogens
1. How do alcohols, phenols, and ethers compare with water and alkanes?
Be able to describe the major differences in properties among members of
these families.
2. What are the distinguishing feature of ethers, sulfur-containing compounds, and
halogen-containing compounds?
Be able to describe the structures and outstanding properties of compounds
with these functional groups.
3. How are alcohols, phenols, ether, sulfur-containing compounds, and halogen-
containing cmpounds named?
Be able to give systematic names for the simple members of these families and
write their structures, given the names.
4. What are the general properties of alcohols and phenols?
Be able to describe such properties as polarity and hydrogen bonding, water
solubility, and boiling points.
5. What are alcohols and phenols weak acids?
Be able to show why alcohols and phenols are acids.
Some Compounds with Oxygen, Sulfur, or Halogen
Ethyl alcohol, dimethyl ether, and propane have similar molecular weights, yet
ethyl alcohol boils more than 100YC higher than the other two.
In fact, the boiling point of ethyl alcohol is close to that of water.
Why should this be?
Alcohols, Phenols, and Ethers
a b
Ethyl Alcohol (CH3CH2OH, Methanol), is one of the oldest known pure organic
chemicals, and it production by fermentation of grain and sugar goes back for
many thousans of years.
Sometimes called grain alcohol, ethyl alcohol is the ͞alcohol͟ present in all
table wines (10-13%), beers (3-5%), and distilled liquors (35-90%).
During fermentation, starches or complex sugars are converted to simple
sugars (C]H12O]) which are then converted to ethyl alcohol:
Some Common Alcohols
Isopropyl Alcohol ((CH3)2CHOH, Isopropanol) or rubbing alcohol, is usedas a
70% mixture with water for rubdowns because it cools the skin through
evaporation and causes pors to close.
It͛s also used as a solvent for medicines, as a sterilant for instrument, and to
cleanse the skin before drawing blood or giving injection.
V Alcohols with two or more ͶOH groups can form more than one
hydrogen bond
V They are therefore higher boiling and water-soluble than similar alcohols
with one ͶOH group.
Chemical Reactions of Alcohols
Dehydration of Alcohols
rlcohls undergo loss of water (dehydration) on treatmen with a strong acid
catalyst. The OH group is lost from adjacent carbon to yield an alkene
product:
Chemical Reactions of Alcohols
Dehydration of Alcohols
rlcohls undergo loss of water (dehydration) on treatmen with a strong acid
catalyst. The OH group is lost from adjacent carbon to yield an alkene
product:
V Methanol and ethanol are no more acidic than water itself and are so
slightly dissociated in water that requir aqueous solution are neutral (pH 7).
V The anion of an alcohol, RO-, known as an alkoxide ion, is a strong base, as
expected for the anion of a weak acid.
V Alkoxides are prepared by reaction of an alcohol with an alkali metal, for
example:
Acidity of Alcohols and Phenols
V Phenols are considerably more acidic than water. Phenol itself (Ka = 1x10-10),
for example, is close to HC (Ka = ]x10-10) and HCO3- (Ka = 5x10-11) in acidity.
V Phenols react as weak Bronsted-Lowry acids with hydroxide ion and are
soluble in dilute aqueous sodium hydroxide.
ames and Properties of Ethers
V Ethers with simple alkyl or aryl groups are named just by identifying the
two groups bonded to oxygen and adding the word ether
V If both groups are the same, the͟di-͟ is often left out and we refer to
͞methyl ether͟ or ͞ethyl ether͟.
V A reference to just ͞ether͟ usually means diethyl ether.
V Compounds containing the COC group in a ring are classified as cyclic
ethers but are not named as such.
ames and Properties of Ethers
V The RO group is reffered to as an alkoxy group; CH3O is a methoxy,
CH3CH2O is an ethoxy group, and so on.
V These names are used when the ether functional group is present with
other functional groups, for example:
V Though polar, ethers lack the hydroxyl group of water and alcohols, and
ether molecules do not hydrogen-bond to each other.
V Thus, the simple ethers are higher boiling point han comparable alkanes
but lower boiling than alcohols.
V The ether oxygen can hydrogen-bond with water, causing dimethyl ether
to be water-soluble and diethyl ether to be partially miscible with water.
V Higher ethers are not only slightly soluble or insoluble in water. Ether are
good solvent for most organic molecules.
Properties of Ethers
Inhalation anesthetics
V Enflurane (trade name Enflurane) and
isoflurane (trade name Forane) are
widely used nonflamable, nonexplosive
anesthetics that produce a rapid
anesthesia from which recovery is also
rapid.
V They are both low-boiling liquids
administered as vapors (enflurane, bp
5].5YC; isoflurane, bp 48.5YC).
Some Common Ethers
V Ethers exist throuhout the plant and animal kingdoms.
V Sme are present in essential oil and are used in perfumes; other have a
variety of biological roles.
V The threemembered epoxide ring in juvenile hormone is quite reactive
because the oxygen and carbon bond angles are highly strained in the
small ring.
[O]
RSSR RSH + RSH
Sulfur bridges in hair. Chemistry can give you curly hair. A permanent wave
results when disulfide bridges are formed between SH groups in hair protein
molecules.
Halogen-containing Compounds
V Halogen-containing organic compounds result from the replacement of
hydrogen atoms by halogen atoms
V The alkyl halide, RX, where R is an alkyl group and X is halogen.
V Their common names are formed by giving the name of the alkyl group
followd by the alogen name with an-ide ending.
V Systematic name for alkyl halides are derived like those of other families
of compounds, by identifying the hydrocarbon root, using the alkane
ending-ane, numbering the halogen substituens, and naming them as
fluoro-, chloro-, bromo-, or iodo- groups.
Some Halogen-containing Compounds
V An iodine-containing hormone secreated by the thyroid gland.
V A deficiency of iodine in the human diet leads to a low thyroxine level,
which causes a condition called goiter and a resulting swelling of the
thyroid gland.
Some Halogen-containing Compounds
V Agricultural use of herbicides such as 2,4-D and fungiside such as Captan
has resulted in vastly increased crop yield and also chlorinated pesticide
of DDT is responsible for the control of malaria and thypus
V But, chlorinated pesticide present problems becausr they are not broken
down by natural processes and persist in the environment.
V They remain in the fatty tissues of organism and accumulate up the food
chain as larger organism consume smaller one.