Organic Chemistry C H H C C H C H H O C

Benzene (C6H6): H C H H C C H C C H C H

2-phenylbutane 3-phenylpropene methylbenzene butylbenzene CH3 - CH2 - CH - CH3 2-phenylbutane CH2 - CH = CH2 3-phenylpropene CH3 CH2 - CH2 - CH2 - CH3 methylbenzene butylbenzene

Most derivatives are the functional group. Organic compounds that replace hydrogen atoms with non-hydrocarbons. Functional groups: Units within organic molecules that are responsible for most of the chemical and physical properties of that molecule. Most derivatives are the functional group.

Alcohols and the Hydroxyl Group

DO Not confuse with the hydroxide ion in inorganic compounds. Functional group in alcohol - hydroxyl group (OH) DO Not confuse with the hydroxide ion in inorganic compounds. NaOH(s) Na+(aq) + OH-(aq) Charged particle attracted to a positively charged ion - dissociates in water. C2H5OH(l) C2H5OH(aq) Covalently bound to a carbon atom in the parent chain - does not dissociate in water

Hydroxyl group makes alcohols polar molecules. General notation for an alcohol is R–OH (R – any hydrocarbon chain) Hydroxyl group makes alcohols polar molecules. Polarity increases IMFs (hydrogen-bonding) – high mp/bp.

O - H O - H CH3 - CH2 - CH2 CH3 - CH2 - CH2 - CH2 - CH - CH3 Only alcohols with up to four carbons are soluble. The non-polar nature of large hydrocarbon chains overcomes the polar nature of the hydroxyl group. δ- δ+ CH3 - CH2 - CH2 O - H δ- δ+ CH3 - CH2 - CH2 - CH2 - CH - CH3 O - H

Alcohols with more than one OH group are named as diols, triols ... Naming Alcohols 1. Identify the parent chain (longest chain with OH) 2. Replace the –e at the end with –ol 3. Number the carbons (hydroxyl has the lowest #) 4. Number the location of the hydroxyl group. 5. Name any alkyl branches (alphabetically) Alcohols with more than one OH group are named as diols, triols ...

CH3 - CH2 - OH Ethanol OH OH Ethandiol CH3 - CH - CH3 2- propanol CH3 drinking alcohol 2- propanol isopropyl alcohol CH3 - CH - CH3 OH CH3 - CH - CH - CH2 - CH - CH3 OH CH3 CH2-CH3 4-ethyl-5-methyl-2-hexanol

Condensed - CH3CH(CH3)CH2CH(OH)CH3 4-methyl-2-pentanol

Glycerol: C3H8O3 (1,2,3 – propanetriol) A sugar alcohol used as an artificial sweetener Major component in fats (triglycerides) Used in pharmaceuticals / personal care products Contains polar bonds Strong IMF between the molecules make glycerol quite thick, like honey.

Phenols -. one hydroxyl group attached to an Phenols - one hydroxyl group attached to an aromatic ring (benzene ring) 2-Methylphenol o-cresol CH3 OH 3-Methylphenol m-cresol 4-Methylphenol p-cresol

hydration reaction C C + H H O H O H H C - C O

H R CH OH Primary Alcohol One R group attached to C-OH. R CH OH Two R groups attached to C-OH Secondary Alcohol R OH C Tertiary Alcohol Three R groups attached to C-OH

Secondary Alcohol CH3 - CH2 - CH2 O - H Primary Alcohol