ࡱ>  %` Ubjbjٕ .(U 4a0FFFFFFF$hZFFFFFFFtttFjFFtFtttF$ S8t10atvttlFFtFFFFF^FFFaFFFF$ Chapter 10 Alcohols I. Structure A. General Formula ROH 1. Hybridization around O atom is 2. Geometry around O atom is B. Classification 4 types (illustrate below) II. Nomenclature A. IUPAC -ane ending changed to ol (parent name based on the longest chain of carbons with the OH group). Ex. 1. 2. 3. B. Common Names name as an alkyl alcohol Ex. 1. 3. 2. 4. III. Physical Properties A. Boiling points Compared to alkanes and ethers, alcohols possess ________ boiling points. Why? Ex. B. Solubility Alcohols are miscible with __________ up to a certain point. The ______ and _____ of R group affects this property. IV. Acid-Base Properties A. For 1o, 2o, and 3o alcohols 1. pKa: R O H pKa range is approx. ______. More basic compared to H2O ( ), RCO2H ( ), and HCl ( ). 2. The acid/base equilibrium reaction: Saw conjugate base (alkoxide ion) being used as a good Nu (in SN2) and a strong base (in E2) 3. Bases for the Deprotonation Good bases for the deprotonation: ___________ and __________ (conjugate acid has higher pKa than alcohol) Poor bases for alkoxide formation: ___________ and ___________ (conjugate acid has lower pKa than alcohol) 4. Alkoxide formation also accomplished by the following redox reaction: B. for phenols 1. pKa: approximately 10. Phenols are _____ acidic than 1o, 2o, and 3o alcohols. Why? 2. The acid/base equilibrium reaction: The conjugate base is called a _________ ____ ( or phenolate ion). Notice stability of it and draw 5 resonance forms here: 3. Base for the deprotonation ___________(____) can be used. In some cases, can also use weaker bases like __________ _________ (_______). V. Synthesis of Alcohols A. from alkyl halides SN2 reaction (REVIEW) B. from alkenes - REVIEW  EMBED StructureOLEServer.Document  KNOW for each reaction above: 1. specific reagents and reaction conditions 2. carbocation intermediate? Rearrangement or no rearrangement? 3. Markovnikov addition or anti-Markovnikov C. from addition reactions of carbanions to carbonyl compounds aldehydes and ketones 1. Nucleophilic addition to carbonyl General concept: Can form 1o, 2o, or 3o alcohols 2. Types of nucleophiles Organometallic Reagents a. Conjugate base of terminal alkyne an organometallic reagent (REVIEW) b. Other Organometallic Reagents - Carbanion nucleophiles 1) Grignard Reagents formation 2) Organolithium reagents formation 3) Examples of Grignard and Organolithium reagents: a. b. c. d. 4) Limitations of organometallic reagents These reagents ________ be used in the presence of molecules with ________ __________. This ____________ the reagent due to ______________ of the ___________________. Ex. 3. Other nucleophiles - Hydride Reagents source of ________ anion KNOW these two reagents 1. NaBH4 in alcohol, ether, or water solvents reduces aldehydes and ketones 2. LiAlH4 reduces aldehydes, ketones, carboxylic acids, and esters to alcohols Ex. a. b. c. 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