Organic Chemistry: ALCOHOLS

ORGANIC CHEMISTRY: WHAT IS IT? ALKENES NAMING ALCOHOLS ALCOHOLS ALCOHOLS H C C C H H H H H OH H Markovnikov's Rule ALKYL HALIDES TO ALCOHOLS SECONDARY ALCOHOL secondary alcohol (2 ): a carbon atom that is attached to TWO alkyl groups and a hydroxyl group PRIMARY ALCOHOL TO ALDEHYDE R OH hydroxyl functional group (-OH) hydrocarbons C H (R) generated from removing an H atom from a water molecule x y one or more hydrogen atoms are removed from the hydrocarbon and replaced with OH group ALDEHYDES KETONES ETHERS C H n 2n (hydration) (oxidization) (oxidization) (dehydration) R-C-H O = R-C-R' O = R-O-R' parent chain and ends with "-ol" main chain must include OH group indicate position of side chains and OH group Multiple hydroxyl groups = polyhydric -C-C-C- - - - - - - - - - - - - - - OH -C-C-C-OH - - - - - - -C-C-C- - - - - - - OH OH (di, tri, tetra, etc.) PREPARATION OF ALCOHOLS alkenes: only contains carbons and hydrogens alkene reacts with a water molecule to make an alcohol a concentrated acid used as a catalyst (ex.H SO ) 4 2 -C-C-C=C + HOH - - - - - - - acid -C-C-C-C- - - - - - - - - OH H ALKYL HALIDES RX (hydration) When halogen halide or water is added to an alkene or alkyne, the H atom bonds with the carbon atom (between the double bond) that initially had more hydrogen atoms -C-C=C- - - - - + HOH acid -C-C-C- - - - - - - OH H PHYSICAL PROPERTIES -OH group attached to the chain makes alcohol more polar PRIMARY ALCOHOL primary alcohol (1 ): a carbon atom that is attached to only ONE alkyl group and a hydroxyl group o -C-C-OH - - - - alkene alkyl halide primary alcohol -C=C- - - + HCl -C-C- - - - - H Cl + HOH -C-C- - - - - H OH + HCl hydrogen halide controlled oxidization with oxidizing agents (ex. KMnO , Cr O ) to supply oxygen atom 4 2 7 2- contains a carbonyl group (CO) attached to an H atom and an alkyl group R-C-H = O -C-C-C-OH - - - - - - + (O) -C-C-C=O + - - - - - HOH an alkene reacted with a halogen halide
an alkane reacted with a halogen halide -C-C-C-C-C- HYDRATION REACTION HYDRATION REACTION - - - - - - - - - - F + HOH -C-C-C-C-C- - - - - - - - - - - OH + HF hydrogen bonds can be formed higher boiling point much more soluble in polar solvents (ex. water) hydrogen bond R-C-OH - - general form: general form: R-C-R' - OH - -C-C-C-C- - - - - - - - - OH ex. ex. forms into a ketone (carbonyl group is formed) o SECONDARY ALCOHOL TO KETONE controlled oxidization with oxidizing agents to supply oxygen atom contains a carbonyl group (CO) with two alkyl groups attached R-C-R' = O -C-C-C-C-C- - - - - - - - - - - OH + (O) -C-C-C-C-C- - - - - - - - - + HOH = O TERTIARY ALCOHOL tertiary alcohol (3 ): a carbon atom attached to a hydroxyl group and three other alkyl groups o general form: R-C-R' - - R" OH -C-C-C-C- ex. - - - - - - - - -C- - - -C- OH Do not oxidize due to no available H atoms to be removed ALCOHOL TO ETHERS formed when two alcohol molecules react a molecule of water is eliminated concentrated sulphuric acid used as catalyst R-O-R' -C-C-C-C-OH + - - - - - - - - HO-C-C-C- - - - - - - acid -C-C-C-C-O-C-C-C- + HOH - - - - - - - - - - - - - - DEHYDRATION/CONDENSATION REACTION DEHYDRATION OF ALCOHOLS removal of water
catalyzed by concentrated sulphuric acid produces an alkene -C-C-C-C- - - - - - - - - OH acid -C-C-C=C- + HOH - - - - - - ALDEYHDE AND KETONE TO ALCOHOL addition reaction with hydrogen (H ) 2 catalyst, high temperatures, and high pressures are needed ALDEHYDE -C-C- - - = O + H-H catalyst heat, pressure -C-C- - - - - H OH KETONE -C-C-C- - - - - = O H-H + heat, pressure catalyst -C-C-C- - - - - - - OH H HYDROGENATION REACTION WORKS CITED general formula: C H OH n 2n + 1