1 2008 Lectures 131415_Alcohols - Chem 2203/2207 Test 2:...

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Chem 2203/2207 Test 2: Tuesday Nov 4, 11:30 -1:00 Surnames A –M Theatre B Surnames N- Z Me 4499 ote: Sample Test 2 posted on Note: Sample Test 2 http://http-server.carleton.ca/~pbuist/ Test 2 covers lecture material on alkyl halides and alcohols. Assignment 4, 5 : alkyl halides, alcohols
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Correction to Slide 51 (previous lecture) - OCH 3 Not . OCH 3
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Alcohols (R OH ) Intro: Alcohols Nomenclature Physical Properties of Alcohols 3 Chemistry of Alcohols Top Ten Reactions
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Alcohols: The Hydroxyl Group Chapter 17 menthol cholesterol cyclohexanol
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Carbohydrates are polyhydroxylated compounds Glucose
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Alcohols = Alkyl or cycloalkyl alcohols (Aromatic Alcohols = Phenols) H cyclohexanol Phenol Estrogen Cholesterol
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Valence of Oxygen • Oxygen has six valence electrons (2 s 2 2 p 4 ) and forms two covalent bonds to complete octet.
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Alcohols are organic derivatives of water: Oxygen is sp 3 hybridized in both water and alcohols Note : This lone pair is behind plane of slide
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Structure Name(IUPAC) Trivial name CH 3 OH methanol methyl alcohol CH 3 CH 2 OH ethanol ethyl alcohol CH 3 CH 2 CH 2 OH 1-propanol n-propanol 2-propanol isopropanol OH 1-butanol n -butyl alcohol 2-butanol* sec -butyl alcohol 2-methyl-2- propanol t -butanol; tert - butyl alcohol 2-methyl-1- propanol OH OH OH OH
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Alcohols can be classified according to the number of carbons attached to the carbon bearing the hydroxyl group 1 ° carbon 3 ° carbon Primary alcohol Secondary alcohol Tertiary alcohol OH OH OH 2 ° carbon
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Some unsaturated alcohols OH Allyl alcohol Benzyl alcohol Propargyl alcohol OH OH
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Stereochemistry! Chiral (stereogenic) centre OH * O H H OH 1 1 4 4 • Non-superimposable mirror images – these are Enantiomers – ( R )-2-butanol and ( S )-2-butanol H 2 2 3 3 Counter clockwise = S Clockwise = R
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Which of these alcohols is chiral? ( R ) or ( S ) at R 1 R 2 CHOH? menthol cholesterol cyclohexanol
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Degrees of Unsaturation of simple alkyl alcohols • Ignore the oxygens in the formula for calculating degrees of unsaturation • CH 4 C n H 2n+2 • CH 3 O H C n H 2n+2 O
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Calculate degree of unsaturation for these alcohols OH Allylic alcohol Benzylic alcohol Propargyl alcohol OH OH
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Physical Properties of Alcohols Recall: Three types of inter molecular interactions affect physical properties: ) an der Waal’s (Induced dipole) 1) Van der Waal’s (Induced dipole) 2) Dipole-dipole interactions 3) Hydrogen bonding Increasing strength of interaction
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• C 1 , C 2 , C 3 alcohols are 100 % water soluble (H-bonding to water); hygroscopic! O H HOH OH 2 HOH . . . . – C 4 alcohols: – n-butanol 10% soluble in water – t-butanol 100% soluble in water – >C4 alcohols water-insoluble. . OH
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This note was uploaded on 07/28/2009 for the course CHEMISTRY CHEM 2203 taught by Professor Levin during the Spring '08 term at Indian Institute of Technology, Chennai.

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1 2008 Lectures 131415_Alcohols - Chem 2203/2207 Test 2:...

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