PowerPoint PresentationSlide 2Slide 3Slide 4Slide 5Slide 6Slide 7Slide 8Slide 9Slide 10Slide 11Slide 12Slide 13Slide 14Slide 15Slide 16Slide 17Slide 18Slide 19Slide 20Slide 21Slide 22Slide 23Slide 24Slide 25Slide 26Slide 27Slide 28Slide 29Slide 30Slide 31Slide 32Slide 33Slide 34Slide 35Slide 36Slide 37Slide 38Slide 39Slide 40Slide 41Slide 42Slide 43Slide 44Slide 45Slide 46Slide 47Slide 48Slide 49Slide 50Slide 51Slide 52Slide 53Slide 54Slide 55Slide 56Slide 57Slide 58Slide 59Slide 60Slide 61Slide 62Slide 63Slide 64Slide 65Slide 66Slide 67Slide 68Slide 69Slide 70Slide 71Slide 72Slide 73Slide 74Slide 75Slide 76Slide 77Slide 78Slide 79Slide 80Slide 81Slide 82Slide 83Slide 84Slide 85Slide 86Slide 87Slide 88Slide 89Slide 90Slide 91Slide 92Slide 93Slide 94Slide 95Slide 96Slide 97Slide 98Slide 99Slide 100Slide 101Slide 102Slide 103Slide 104Slide 105Slide 106Slide 107Slide 108Slide 109Slide 110Slide 111Slide 112Slide 113Slide 114Slide 115Slide 116Slide 117Slide 118Slide 119Slide 120Slide 121Slide 122Slide 123Slide 124Slide 125Slide 126Slide 127Slide 128Slide 129Slide 130Slide 131Slide 132Slide 133Slide 134Slide 135Slide 136Slide 137Slide 138Slide 139Slide 140119.13) Which of the following bases are strong enough to deprotonate CH3COOH?a) F-b) (CH3)3CO-c) CH3-d) NH2-e) Cl-pka of CH3COOH is 4.8.b) has a pka of 18c) has a pka of 50d) has a pka of 38 pka of conjugate acid must be greater than that of the carboxylic acid being deprotonated.219.14) Rank the labeled protons in order of increasing acidity.OHcOHOHbHaHa<Hb<HcThe more stable the conjugate base the more acidic the proton.319.15) Match each pka value with each carboxylic acid.(3.2, 4.9 and 0.2)a) CH3CH2COOHb) CF3COOHc) ICH2COOH4.90.23.2Electron withdrawing groups make acids more acidic.419.16) Why is formic acid more acidic than acetic acid?HOHOOHOThe methyl group is electron donating and stabilizes the acid while destabilizing the conjugate base thus making it less acidic.519.17) Rank the compounds within each group in order of decreasing acidity.a) CH3COOH, HSCH2COOH, HOCH2COOH3 2 1b) ICH2COOH, I2CHCOOH, ICH2CH2COOh 2 1 3619.18) Rank each group of compounds in order of decreasing acidity.a)CO2HCO2HClCO2H2 1 3b)CO2HCO2HCO2HH3COO 2 1 3719.19) Is the following compound more or less acidic than phenol? HOOHRThe more electron donating groups present, the less acidic a compound is. This compound has an additional hydroxy and alkyl group, both electron donating. So it is less acidic.819.22) Comparing CF3SO3H and CH3SO3H, which has the weaker conjugate base? Which conjugate base is the better leaving group? Which of these acids has the higher pka?CF3SO3H is the weaker conjugate base.CF3SO3H is the better leaving group because it is the weaker conjugate base.CH3SO3H, with the electron donating methyl group, has the higher pka and is thus a weaker acid.9Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and ReductionTwo broad classes of compounds contain the carbonyl group:Introduction[1] Compounds that have only carbon and hydrogen atoms bonded to the carbonyl[2] Compounds that contain an electronegative atom bonded to the carbonyl10•The presence or absence of a leaving group on the carbonyl determines the type of reactions the carbonyl compound will undergo.•Carbonyl carbons are sp2 hybridized, trigonal planar, and have bond angles that are ~1200. In these ways, the carbonyl group resembles the trigonal planar sp2 hybridized carbons of a C=C.11•In one important way, the C=O and C=C are very different.•The electronegative oxygen atom in the carbonyl group means that the bond is polarized, making the carbonyl carbon electron deficient.•Using a resonance description, the carbonyl group is represented by two resonance structures.12Carbonyls react with nucleophiles.General Reactions of Carbonyl Compounds13Aldehydes and ketones react with nucleophiles to form addition products by a two-step process: nucleophilic attack followed by protonation.14•The net result is that the  bond is broken, two new  bonds are formed, and the elements of H and Nu are added across the  bond.•Aldehydes are more reactive than ketones towards nucleophilic attack for both steric and electronic reasons.15Carbonyl compounds with leaving groups react with nucleophiles to form substitution products by a two-step process: nucleophilic attack, followed by loss of the leaving group.The net result is that Nu replaces Z, a nucleophilic substitution reaction. This reaction is often called nucleophilic acyl substitution.1617•Nucleophilic addition and nucleophilic acyl substitution involve the same first step—nucleophilic attack on the electrophilic carbonyl carbon to form a tetrahedral intermediate.•The difference between the two reactions is what then happens to the intermediate.•Aldehydes and ketones cannot undergo substitution because they do not have a good leaving group bonded to the newly formed sp3 hybridized carbon.18•Carbonyl compounds are either reactants or products in oxidation-reduction reactions.Preview of Oxidation and Reduction19The three most useful oxidation and reduction reactions of carbonyl starting materials can be summarized as follows:20•The most useful reagents for reducing aldehydes and ketones are the metal hydride reagents.Reduction of Aldehydes and Ketones•Treating an aldehyde or ketone with NaBH4 or LiAlH4, followed by H2O or some other proton source affords an alcohol.21•The net result of adding H:¯ (from NaBH4 or LiAlH4) and H+ (from H2O) is the addition of the elements of H2 to the carbonyl  bond.22•Catalytic hydrogenation also reduces aldehydes and ketones to 1° and 2° alcohols respectively, using H2 and a catalyst.•When a compound contains both a carbonyl group and a carbon—carbon double bond, selective reduction of one functional group can be achieved by proper choice of the reagent.A C=C is reduced faster than a C=O with H2 (Pd-C).A C=O is readily reduced with NaBH4 and LiAlH4, but a C=C is inert.23•Thus, 2-cyclohexenone, which contains both a C=C and a C=O, can be reduced to three different compounds depending upon the reagent used.24•Hydride converts a planar sp2