CHEM 102 Chapter 5 Lecture 12 Outline of Last Lecture I. Addition Reactions & Combustion Reactions of Alkenesa. Definition; Is it symmetric or asymmetricII. Cycloalkenes as cis/trans isomersa. How to tell which it isIII. Order of Carbon atomsa. Primary, Secondary, Tertiary, Quaternary b. How stable each atom is according to its orderIV. Carbocationsa. Definitionb. What happens when they react with symmetric or asymmetric reagents V. Markvnikov Rulea. DefinitionVI. Alkynesa. Definitionb. NamingVII. Aromatic Compoundsa. Definitionb. NamingOutline of Current Lecture These notes represent a detailed interpretation of the professor’s lecture. GradeBuddy is best used as a supplement to your own notes, not as a substitute.I. Structure of AlcoholsII. Bonding in AlcoholsIII. Constitutional Isomers and /naming AlcoholsIV. Physical Properties of AlcoholsV. Oxidation and Dehydration of AlcoholsVI. Recognizing PhenolsVII. Recognizing EthersVIII. Naming EthersCurrent LectureStructure of AlcoholsAlcohol – compound with at least one (1) OH group*General formula = R – OH where R is an aliphatic* EX. CH3 – OH *Alcohols always have a tetrahedral shape and have a bond angle of 109 degrees.*Constitutional Isomers for Alcohol – Can have different carbon skeletons, as usual, and can have different placement of the OH group EX. Page B60 in BookClassifying and Naming Alcohols – find the OH group and see what kind pf carbon it is on (primary, secondary, tertiary, etc.) and that is the classification of the Alcohol. So you can have a primary alcohol, secondary alcohol or tertiary alcohol.*To name an Alcohol name is the same way we’ve been doing but put an –ol one the end in stead of the –e . Also, the OH group always gets the smallest number. * EX. Butane  Butanol REMEMBER THE ALCOHOL GLYCEROL/GLYCERIN ( AKA 1,2,3 propanetriol) *If you come upon a question that is an Alkene and an Alcohol (yes it is possible), remember to name the OH group with the smallest number, but put the alkene’s name first (like pentene), then put –ol on the end. Remember to name it as cis or trans Ex. Trans – 1- Pentene- 1 – OLRemember the Physical Properties of Alcohols ( Table Below) Make flashcardsName Formula MP BP( boiling point in celcius)Methanol CH3 OH -97 C 65 C Ethanol CH3CH2OH -224 C 78 C1-Propanol CH3CH2CH2OH -126 C 97 C1-Butanol CH3CH2CH2CH2OH -90 C 118 C1-Hexanol CH3CH2CH2CH2CH2CH2OH -52 C 158 C1-Octanol CH3CH2CH2CH2CH2CH2CH2CH2OH -16 C 194 C*Alcohols have much higher melting and boiling points, they are soluble in water, and are attributed to hydrogen bonding*Acidity and Basicity of Alcohols – Alcohols are very close to neutral but can act like acids and bases at times. They will react with an acid and accept a proton, but they will also react with a base and donate a proton.*Addition reactions with an alkene and water creates alcohols* Ex. Ethene + H2O = EthanolDehydration reactions- Basically, in a dehydration reaction, you are taking the water from an alcohol, and adding a double bond. After the double bond is added and the water is taken away,the compound is no longer an alcohol, but an alkene or an Ether. *Dehydration in the presence of an acid at temperatures 180 degrees and above produce alkenes *Dehydration in the presence of an acid at temperatures 140 degrees and below will produce Ethers *The major product I formed from the more stable carbocation (if the double bond was formed on a primary, secondary, tertiary, or quaternary carobn)*Oxidation Reactions - Adding on Oxygen to the compound *Mild Oxidation first leads to an aldehyde for primary alcohols, then to carboxylic acid *For secondary alcohols, oxidation lead to a ketone *Oxidation of a tertiary alcohol is impossible*Combustion Reactions – leads to the formation of CO2 and H2O, just like AlkanesPhenols – Remember that Benzene is a phenol. Alcohol- like compounds that have a hydroxyl group bound to a benzene ring. Make flashcards of the aromatics we needed to remember, you will need them for naming phenols. *To name phenols, you must look at the aromatic. Aromatics have a different naming system. You use ortho, meta, and para ( See below) https://www.google.com/search?hl=en&site=imghp&tbm=isch&source=hp&biw=1517&bih=714&q=ortho+meta+para+directors&oq=ortho%2C+meta+para+&gs_l=img.1.2.0l5j0i24l5.1328.6733.0.9310.17.17.0.0.0.0.161.1242.15j2.17.0....0...1ac.1.55.img..0.17.1239.E5-dnOX57IA#facrc=_&imgdii=_&imgrc=wJGopcWN5xVLrM%253A%3BVZC9zvxKQLJVpM%3Bhttp%253A%252F%252Fchemwiki.ucdavis.edu%252F%2540api%252Fdeki%252Ffiles%252F2286%252Fimage-3.jpg%253Fsize%253Dbestfit%2526width%253D432%2526height%253D157%2526revision%253D1%3Bhttp%253A%252F%252Fchemwiki.ucdavis.edu%252FOrganic_Chemistry%252FHydrocarbons%252FAromatics%252FProperties_of_Aromatics%252FInductive_Effects_of_Alkyl_Groups%3B550%3B231So instead of putting a number where the methyl group is, you’ll put ortho, meta, or para EX. Meta methyl phenol or m-methyl phenolEthers – compounds where both sides of the oxygen is bound to an alkyl or aryl group. R-O-R R= Alkyl or Aryl *Properties of Ethers- Less polar than alcohols- Not soluble in water- Lower MP and BP than alcohols- Chemically inert- VERY flammable2 Ways of Naming EthersCommon – treats each carbon chain as a branch off the oxygen. List each side with a –yl ending and add Ether to the end of the name. Ex. C – O – C – C This is called Ethyl Methyl Ether because it has a methyl group (blue) and an Ethyl group (yellow) coming off the oxygen. IUPAC – Same thing we have been doing. Use the parent chain name as the base with an –ane ending. Find the groups with –yl ending, if it has and oxygen attached to it as well, end the name with –oxy instead of –yl.