Download Hydrocarbon Derivatives

Hydrocarbon Derivatives
 molecular compounds of carbon and hydrogen that
contain at least one other element.
 ex) alkyl halide, alcohol, carboxylic acid, ester
Alkyl Halides
 one or more hydrogen atoms are replaced with a halogen
(F, Cl, Br, I).
 Many of these are carcinogenic or toxic.
 Compounds include CFC’s, Teflon coatings and
insecticides.
Naming Organic Halides
 number parent chain from end closest to halogen, for
a cycloalkane, start numbering at halogen
 use shortened names, put in alphabetical order and use
prefixes as needed: bromo, chloro, fluoro, and iodo.
 name and number alkyl groups
 Ex. 1,2-dichloroethane
Alcohols
 contain an hydroxyl (-OH) functional group-is polar
 higher boiling point than alkanes because of hydrogen bonds.
Chains up to 12 C are liquid.
 short chain alcohols (methanol,ethanol) are very soluble in
water due to polarity
 Longer chains become more non polar and do not dissolve in
water but with non polar compounds
Naming Alcohols
 name alkanes but replace the ending –e with the ending
–ol unless there is a prefix then leave the –e and add –ol
after prefix
 number closest to the OH
 the position of the OH group(s) is indicated with a
number(s) before the –ol.
 use prefixes to indicate the number of OH groups
 name and number alkyl groups
Examples
 ethanol
 2-methylpropan-2-ol
 propane-1,2,3-triol
 rubbing alcohol
propan-2-ol
Carboxylic Acids
 contain a carboxyl (- COOH)
 carboxyl is polar, easily form hydrogen bonds.
 higher boiling points than other hydrocarbons and
derivatives
 short chains are liquids and soluble in water, longer
chains are waxy solids and not soluble
 hydrogen on the hydroxyl is acidic.
 found in sour fruits and vinegar
 Ex. Ethanoic acid = vinegar
Naming Carboxylic Acids
 Replace the alkane ending, –e, with the ending -oic acid.
 Carboxyl is position 1
 Name and number alkyl chains
 Ex. butanoic acid
 Some carboxylic acids have more than one carboxylic acid group, so
they are given common names
 Ex) oxalic acid and citric acid.
Esters
 functional group is similar to carboxyl except that the hydrogen
on the hydroxyl is replaced with a carbon chain.
 responsible for the smells of many fruits and vegetables
(volatile so create aromas)
 without an –OH group, can not make hydrogen bonds so
boiling points are lower than carboxylic acids
 Small esters are liquids, larger are waxy solids
 4 carbons or fewer are soluble, larger are not soluble in water
 formed when a carboxylic acid reacts with an alcohol
Naming Esters
Two parts:
 The name from the acid (contains C=O) is changed from
–oic acid to –oate and is the main chain (name last)
 The name of the alkyl group from the alcohol ends in –yl
and is given first.
 Example: ethyl ethanoate