Chemistry 211 - Review Sheet for Exam #1

As a guide for studying, you should be familiar with the concepts listed below. Know reaction mechanisms for reactions of organometallic compounds with aldehydes, ketones, and esters, and the reactions involving alchols and ethers.  To review naming information, go to the Organic Nomenclature page.

Chapter 14: Organometallic compounds Organolithium compounds (R-Li) Grignard reagents (R-MgX) Carbanions Brønsted bases pKa values (approximate) Alkane ~ 60 NH3 ~ 36 ethyne ~ 26 alcohol - 16 water - 15.7 ketone enolate ~16-20 b-keto esters ~11 Grignard synthesis of alcohols 1o - from formaldehyde 2o - from any other aldehyde 3o - from ketones Grignard reaction mechanism Organolithium synthesis of alcohols Acetylenic alcohols Retrosynthetic analysis Reactions with esters - 3o alcohols Alkane synthesis with organocuprates

Chapter 15: Alcohols Acid-catalyzed hydration of alkenes Hydroboration-oxidation of alkenes Hydrolysis of alkyl halides Grignard reaction with aldehydes & ketones Grignard reaction with esters Reduction of aldehydes & ketones LiAlH4 & NaBH4 Reduction of carboxylic acids & esters Alcohols from epoxides Preparation of diols Conversion of alcohols to ethers Carboxylic acids Acyl chlorides Acid anhydride Fischer Esterification Esters of inorganic acids Oxidation of alcohols Chromic acid Pyridinium chlorochromate (PCC) Pyridinium dichromate (PDC) Biological oxidation of alcohols NAD+ (biological oxidizing agent)

Chapter 16: Ethers Nomenclature  Oxirane (ethylene oxide) Tetrahydrofuran Structure of ethers Physical properties of ethers Preparation of ethers H+ catalyzed reaction of alkenes and alcohol Williamson ether synthesis H+ catalyzed cleavage of ethers Reactions of epoxides Miscellaneous Transition states nucleophiles electrophiles Substitution reactions Addition reactons Resonance structures Oxidation - reduction Lewis acids & bases Brønsted-Lowry acids Synthesis Resonance

For more information, go to Chem211 Exam #1 Sample Test page.