Alcohol and Phenol in Organic Chemistry Lecture, Study notes of Organic Chemistry

Download Alcohol and Phenol in Organic Chemistry Lecture and more Study notes Organic Chemistry in PDF only on Docsity! ALCOHOL Common name: alkyl + alcohol ● For simple alkyl groups only IUPAC Name ● Open chain alcohols 1. Locate longest carbon chain. Change -e suffix to -ol. 2. Number parent chain beginning with carbon end na closest to -OH group. 3. Number substituents ● Cyclic alcohol 1. Ring bearing -OH ang parent ring. 2. Position 1 is carbon bearing -OH but position 1 is not in the name. 3. Lowest numbering of substituents. Polyol ● 2 or more -OH groups 1. Alkane name + diol, triol etc. Enol / Ynol ● Double / triple bond on parent chain 1. Name parent chain as alkene / alkyne. 2. Drop -e suffix, add position number of -OH, add -ol. 3. Lowest numbering where -OH is priority. =" Nucleophilic Substitution Reactions * -OH group is a poor leaving group v must be protonated first * a-carbon is electrophilic Y canbe attacked by the Ne nucleophile actions of Alcohols = Nucleophilic Substitution Reactions ton eS —cC—Nu + H20 General Equation Common Reagents: HCI/ZnCl2, SOCI2, POCI; & PCI; for 1°and 2° ROH, HCI for 3° alcohols, HBr, HI, or MX/HSO, for 1°, 2°, and “S. 3°ROH. actions of Alcohols = Nucleophilic Substitution Reactions 2. Reaction with HX X20 ‘o R7 “Ht HX — pe H H + REACTIVITY: HI > HBr > HCI (uses ZnCl, as catalyst) (Weakest Bond, more reactive) * 3°ROH: reacts via Sy1 * 1° and 2°: more resistant to reaction with HX $y2: 12 ROH with HX Hq Hq 1 aé< fast | (1) R—-E—OH + H == = R-c-0@ H H Ul a H R H | las N+ RE —o@ HM | Nur SO | REN + HO a OH i Syl: 22 and 32 ROH with HX R" R" i ao fast ee (4) R-¢c—OH + HO ==> R—C—0@ Rg H oxonium ge R* PH slow 1 g Rc === RCO a af . carbocation: prone to rearrangement a R" R | ‘ (3) NUP + oer —_ Rpt R' rR c—cl + Ch OH 3° alcohol racemio mixture CHgCHp 8 CH,CHyy 2 te ICH HCI isCHa, HCH Syt Se a ~ = ae + H,0 Reactions of Alcohols = Nucleophilic Substitution Reactions 3. Reaction with PX3 “ x “oO! R os + :PX; ——> R7 * XP ~ ° PX3: PBrg or Pls * reacts via Sy2 (no rearrangement) ¢ 4° and 2° alcohols are more reactive ~ Reactions of Alcohols = Nucleophilic Substitution Reactions 3. Reaction with SOCI, aya adi ° ° Roos ¢ SOC Pe ro + Ns=o * cf * reacts via Sy2 (no rearrangement) * 1° and 2° alcohols are more reactive rin Elimination Reaction