Organic Chemistry Reactions for Exam 2 (CH232, Summer 2007) - Prof. Silas Blackstock, Exams of Organic Chemistry

Download Organic Chemistry Reactions for Exam 2 (CH232, Summer 2007) - Prof. Silas Blackstock and more Exams Organic Chemistry in PDF only on Docsity! List of Reactions for Exam 2 (CH232, summer 2007) * = mechanism covered chapter 17 - alcohols - material relevant to carbonyl chemistry * aldehyde reduction with NaBH4 or LiAlH4 to 1˚ alcohol * ketone reduction with NaBH4 or LiAlH4 to 2˚ alcohol * ester reduction with LiAlH4 (2 equiv) to 1˚ alcohol Grignard reagent formation from RX + Mg in ether solvent * Grignard reagent addition to formaldehyde to form 1˚ alcohols (homologation rxn) * Grignard reagent addition to aldehydes to form 2˚ alcohols * Grignard reagent addition to ketones to form 3˚ alcohols * Grignard reagent addition to esters (twice) to form 3˚ alcohols * Grignard reagent addition to CO2 to form carboxylic acids (homologation rxn) * phenol preparation by cumene oxidation/hydrolysis * 1˚ alcohol oxidation with Jones reagent (H2CrO4) to make carboxylic acids * 1˚ alcohol oxidation with PCC (pyridinium chlorochromate) to make aldehydes * 2˚ alcohol oxidation with Jones reagent (or PCC) to make ketones * alcohol conversion to silyl ether with TMS chloride/pyridine (reversible protection/deprotection) chapter 18 - ethers, epoxides, sulfides * Williamson ether synthesis NaOR + 1˚R´X = ROR´ (SN2) ether formation by alkoxymercuration/demercuration of alkenes * epoxidation of alkenes with peracids (RCO3H, specifically mCPBA) * epoxide formation by halohydrin formation/deprotonation * ether cleavage by strong acids (HBr or HI) * Claisen rearrangement of allyl vinyl ethers or allyl aryl ethers * epoxide ring opening - acidic conditions * epoxide ring opening - basic conditions (SN2) * thiol formation via thiourea alkylation with RCH2Br / hydrolysis * sulfide formation via thiolate alkylation (SN2) * disulfide formation via thiol oxidation with I2 or Br2 disulfide cleavage to thiols via Zn,H+ * sulfide oxidation with H2O2 or RCO3H to sulfoxides * sulfoxide oxidation with RCO3H to sulfones chapter 19 - aldehydes and ketones * aldehyde formation via 1˚ alcohol oxidation with PCC,CH2Cl2 (ch 17) aldehyde formation via DIBAH reduction of esters * aldehyde or ketone formation via alkene ozonolysis (ch 7) * ketone formation via 2˚ alcohol oxidation with PCC,CH2Cl2 or Jones reagent (ch 17) * aryl ketone formation via Friedel-Crafts acylation (ch 16) methyl ketone formation via HgII catalyzed hydration of terminal alkynes (ch 8) ketone formation via cuprate reaction with acid chlorides * aldehyde oxidation to carboxylic acids via Jones oxidation (aq H2CrO4) * reversible hydration of aldehydes and ketones (acid or base catalyzed) * cyanohydrin formation from aldehydes or ketones via addition of HCN * alcohol formation from aldehydes or ketones via hydride (NaBH4 or LiAlH4) or Grignard reagent additions * imines from aldehydes or ketones via reaction (condensation) with 1˚ amines * enamines from aldehydes or ketones via reaction (condensation) with 2˚ amines * Wolff-Kishner reduction of aldehydes or ketones with hydrazine, NaOH, ∆ Clemmenson reduction of aldehydes or ketones with Zn, H+ * acetal formation (reversible) of aldehydes or ketones by rxn (condensation) with alcohols (C=O protection) * Wittig reaction of aldehydes or ketones with phosphonium ylides to form alkenes * Wittig reagent (phosphonium yilde) formation from (1) RX, Ph3P / (2) nBuLi * conjugate addition of 1˚ and 2˚ amines to α,β-unsaturated ketones or aldehydes conjugate addition of organocuprates to α,β-unsaturated ketones or aldehydes