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 106120.8) Draw the products when the following compounds are treated with NaBH4 in MeOH.a)ONaBH4MeOHHO H+OHHb)ONaBH4MeOHOHc)(H3C)3C ONaBH4MeOH(H3C)3C OH+(H3C)3C OH220.9) What reagent is needed to carry out the reaction below?OClHOClHTwo reagents are needed to carry out this reaction. First, the (S)-CBS reagent to produce the R-enantiomer. Followed by H2O to protonate the alcohol.320.12) Draw the products of LiAlH4 reduction of each compound.a)OHOOHb)NH2ONH2c)ON(CH3)2N(CH3)24d)NHONH520.14) Predict the products of these compounds when treated with the following reagents.a) O OOCH3LiAlH4H2ONaBH4MeOHOHOHOH OOCH3b)OHOOH3COLiAlH4H2ONaBH4MeOHHO OHNo reaction6c)LiAlH4H2ONaBH4MeOHH3CO OH3CO OHH3CO OH720.15) Predict the products in the following reactions.a)OHAg2ONH4OHNa2Cr2O7H2SO4, H2OOHONo Reactionb)Ag2ONH4OHNa2Cr2O7H2SO4, H2OOH OOH OOHO OOH820.16) Predict the products of the compound below when reacted with each reagent.HOOHOa)NaBH4MeOHHOOHOHb)LiAlH4H2OHOOHOH9HOOHOc)PCCOOOd)Ag2ONH4OHHOOH OOHe)CrO3H2SO4, H2OHOO OOHO1020.22) Draw the products (including stereochemistry) of the following reactions.a)H3COHH3CH2C MgBrH2OH OHH OH+b)OH3CH2C LiH2OOHCH2CH3OHCH2CH3+1120.26) Draw out the products when each compound is treated with 2 equivalents of CH3CH2CH2CH2MgBr followed by H2O?a)H3CH2COClH3CH2COHCH2CH2CH2CH3CH2CH2CH2CH3b)OOCH3HOCH2CH2CH2CH3CH12CH2CH2CH3c)OOCH2CH3H3CH2CH2CH2CH2COHCH2CH2CH2CH3H3CH2CH2CH2CH2CCH2CH2CH2CH31220.28) Tertiary alcohols can also be formed by reacting dimethyl carbonate with excess Grignard reagent. Draw out a mechanism for the following reaction. C6H5MgBr+OH3CO OCH3H2OOHC6H5C6H5C6H5+MeOH+ HOMgBrOH3CO OCH3MgBrOH3CO OCH3+ MgBrOH3COMgBr+ OCH313OOCH3+ MgBrOMgBr+ OCH3O+ MgBrHO HOH+ HOMgBr+ HOCH31420.32) What carboxylic acid is formed from each aqlkyl halide when treated with Mg, CO2 and H2O?a)BrMgMgBrCO2OOH2OOOH15b)MgH3CH2CH2CH2C ClCO2H3CH2CH2CH2C MgClOOH3CH2CH2CH2CH2OOOHH3CH2CH2CH2Cc)OCH3CH2BrMgOCH3CH2MgBrCO2OCH3COOH2OOCH3COOH1620.34) Draw the products of each compound when treated with either dimethylcuprate or lithium acetylide followed by water.a)OCuLiH2OCLiH2OOHO17b)CuLiH2OCLiH2OH3CH2COCH2CH3H3CH2COCH2CH3H3CH2COHCH2CH318c)CuLiH2OCLiH2OOOHO1920.35) What reagents are needed in each reaction?a)OOCuLiH2Ob)OOHLiH2Oc)OOHCuLiH2OLiH2O2020.36) Synthesize each of the following using cyclohexanol, ethanol and any other inorganic reagent.a)OHOHHBr or PBr3BrMgMgBrPCCOHOMgBrH2OHO21b)BrHOHBrBrc)HOH2SO4+H2Pd-C22d)OOHHBr or PBr3BrMgMgBrOHPCCOH2OHOPCCO23OHH2SO4e)OHm-ClPBAOMgBr+H2OOH24Aldehydes and ketones contain a carbonyl group. An aldehyde contains at least one H atom bonded to the carbonyl carbon, whereas the ketone has two alkyl or aryl groups bonded to it.IntroductionTwo structural features determine the chemistry and properties of aldehydes and ketones.Aldehydes and Ketones—Nucleophilic Addition25•Aldehydes and ketones react with nucleophiles.•As the number of R groups around the carbonyl carbon increases, the reactivity of the carbonyl compound decreases, resulting in the following order of reactivity:IntroductionAldehydes and Ketones—Nucleophilic Addition26•If the CHO is bonded to a chain of carbons, find the longest chain containing the CHO group, and change the –e ending of the parent alkane to the suffix –al. If the CHO group is bonded to a ring, name the ring and add the suffix –carbaldehyde.•Number the chain or ring to put the CHO group at C1, but omit this number from the name. Apply all the other usual rules of nomenclature.Nomenclature of Aldehydes27•Like carboxylic acids, many simple aldehydes have common names that are widely used.•A common name for an aldehyde is formed by taking the common parent name and adding the suffix -aldehyde.•Greek letters are used to designate the location of substituents in common names.28•In the IUPAC system, all ketones are identified by the suffix “one”.•Find the longest continuous chain containing the carbonyl group, and change the –e ending of the parent alkane to the suffix -one.•Number the carbon chain to give the carbonyl carbon the lowest number. Apply all of the usual rules of nomenclature.•With cyclic ketones, numbering always begins at the carbonyl carbon, but the “1” is usually omitted from the name. The ring is then numbered clockwise or counterclockwise to give the first substituent the lower number.Nomenclature of Ketones29•Most common names for ketones are formed by naming both alkyl groups on the carbonyl carbon, arranging them alphabetically, and adding the word “ketone”.•Three widely used common names for some simple ketones do not follow this convention:30•Sometimes, acyl groups must be named as substituents. The three most common acyl groups are shown below:31•Aldehydes and ketones exhibit a strong peak at ~1700 cm-1 due to the C=O.•The sp2 hybridized C—H bond of an aldehyde shows one or two peaks at ~2700 –2830 cm-1.Spectroscopic Properties—IR SpectraFigure 21.3The IR spectrum ofpropanal, CH3CH2CHO32•Most aldehydes have a carbonyl peak around 1730 cm-1, whereas for ketones, it is typically around 1715 cm-1.•Ring size affects the carbonyl absorption in a predictable manner.33•Conjugation also affects the carbonyl absorption in a predictable manner.Figure 21.4The effect of conjugation onthe carbonyl absorptionin an IR spectrum34Aldehydes and ketones exhibit the following 1H and 13C NMR absorptions.Spectroscopic