ReviewLewis StructureConstitutional IsomerismResonance StructuresPhysico-chemical PropertiesPhysico-chemical PropertiesSlide Number 7Slide Number 8Slide Number 9Write the StructuresIUPAC NamingIUPAC NamingComplete ReactionSlide Number 14Slide Number 15Isomerism (2)StereoisomerismReactionsReactionsReactionsReactionsReactionsSlide Number 23ReactionsReactionsCompound A has the formula C6H14O. It reacts with sodium metal to produce H2 gas. It reacts with H2SO4 to produce compound B. Compound A is formed by the reaction compound B with BH3/THF followed by reaction with H2O2/NaOH. Mass spectraSlide Number 28ReactionsReactionsSlide Number 31Slide Number 32Multi-step SynthesisMulti-step SynthesisSlide Number 35Slide Number 36Review CIOS Survey: 28.8%Lewis Structure For each of the following arrangement of atoms (a) draw a correct Lewis structure and (b) indicate the formal charge associated with each of the atoms. COHOformic acidHNNNazide ion_Constitutional Isomerism • Draw a constitutional isomer for each of the following. C CCH3HH3CHH3CH3CHHC CCH3CHHCCHC CC CCH3H3CThese are example of constitutional isomers—others are possibleResonance Structures BenzaldehydeOHOHOHOHPhysico-chemical Properties • Which of the following molecules will have the largest dipole moment? HCF3HH3CHCH2FFH2CHFCH3H3CFHCH3H3CH(1) (2) (3) (4)Physico-chemical Properties • Which of the following molecules has the highest boiling point? OHHOOHO(4) (2) (3) (1)HCNOHCHOThe following transformation can be classified as: (1) an elimination (2) a substitution (3) a rearrangement (4) an addition (CH3)3COHHClFFK+ Cl-++(CH3)3COH(CH3)3CO- K+C2H5C2H5+The following transformation can be classified as: (1) an elimination (2) a substitution (3) a rearrangement (4) an addition CCCHClHH3COO+C2H5O- Na+CCCHClHC2H5OO+CH3O- Na+Write the Structures bicycle[2,2,1]heptane iso-butylcycloheptane 3-chloro-3-methyloctan-2-ol OHClIUPAC Naming FF4-ethyl-2,3-difluoroheptaneC2H51-ethylcycloocta-1,5-dieneClCH3CH3FCH3H3CIUPAC Naming 2-chloro-3-fluoro-2,3-dimethylbutaneComplete Reaction CCH+Na+ NH2-Liquid AmmoniaCH3CH3CCCH3CH3NaH3CH+H2PdCH3CH2OH25o, 1 atm.CH3CH3H3CHCH3CH3HHCH2H2CCOHOBrH3CCOCH2BrOHCCH2OCH2BrOH2CCH2COBrHOIR MS 1H NMR 13C NMR C5H8O MW=84 OIsomerism (2) CH3HClCH3HClCH3ClHCH3HClCH3HClBrHPhHH3CClBrPhHDiastereoisomers EnantiomersStereoisomerism CH3BrBrHHC2H5(2S,3R)-2,3-dibromopentaneCOC2H5H3CCH3(2-ethoxypropan-2-yl)benzene(H3C)2HCCC(CH3)3C2H5CH3(S)-3-ethyl-2,2,3,4-tetramethylpentaneAssign R or S configuration to chiral centers in molecules below:Reactions H2CCOCH2OCH3Na+ I-AcetoneBrH2CCOCH2OCH3I+ NaBrOBrNa+ CN-Ethanol-WaterO CN+ NaBrOOCH3CH3H2CHOO2SNa+ I-AcetoneOOCH3CH3IH2CHSO3Na+Reactions OHOCH3H3COH3COSO2ClH3C+N(1)(2)Li+ I-, AcetoneIOCH3H3COH3COClClNa+ I- (1 mole), AcetoneC5H10IClC CBrBrHHHHH2C CH2S-Na+Na+S-C4H8S2ReactionsReactions CC(1) Li, CH3CH2NH2, -78oC(2) NH4ClH3CCCH3CHHBrCCC(CH3)3H3C CH3H H(CH3)3CO- K+(CH3)3COHCCC(CH3)3H2CCH3H HReactions (1) Hg(O2CCH3)2, H2O(2) NaBH4, NaOHH3CH3CHOCCHH3CC2H5H(1) OsO4(2) NaHSO3, H2OCCHH3CC2H5HOH OH+ enantiomerCH3CCH3CCH3H3C(1) O3, CH2Cl2, -78oC(2) Zn/HOAc+(CH3)2COPCl5(1) NaNH2, liq. NH33 equivalents(2) CH3BrH2, Pd/CaCO3quinoline(1) OsO4, pyridine(2) NaHSO3, H2O(CH3)3CO-K+CCC(CH3)3H3CHHC1 moleOHHOCHCl3H3C CH3CH3CCH3CCH3H3COCH3CCH3CCH3H3CClClCH3CCH3H3CH3CCH3CCH3H3CH3CHHCH3CCH3H3CH3CHHCl ClReactions CH3CH2O- Na+CH3CH2OHClHHCH(CH3)2HH3CHCH(CH3)2HH3CReactions 85% H3PO4(H3C)3C CHCH3OHCH3CH3H3CH3COHCH3CH3HOH3CCH385% H3PO4OCH3H3CCH3CH3Compound A has the formula C6H14O. It reacts with sodium metal to produce H2 gas. It reacts with H2SO4 to produce compound B. Compound A is formed by the reaction compound B with BH3/THF followed by reaction with H2O2/NaOH. A) B)Mass spectra A) B) 84 43 56 69 69 84 C6H14O 56 41CH2H3CCH3CH3CH2CH2H2CH3C CH368 41 69 41 56 H2CHCCH2CHCH3CH369 56 43Reactions CCH2HBrCCH3BrH2O, H2SO4CH3OHH+ enantiomerReactions H2O, H2SO4HgSO4OHOC CHH3CHBr, darkH3CBr HHC CHH3CHBr, peroxideBrHHH3CHow would you carry out each of the following transformation. You may use any organic or inorganic reagents. Pay attention to the regiochemistry and stereochemistry associated with reactions in your proposed sequence. H HCH3HOHCH3HOH1)NaNH22)CH3IH3CH1)NaNH22)CH3IH3CHH2/PtHCH3HH3CKMnO4/cold/diluteHow would you carry out each the transformation(R)-3-bromo-2,2-dimethylbutane to 3,3-dimethylbutan-1-ol. You may use any organic or inorganic reagents. Pay attention to the regiochemistry and stereochemistry associated with reactions in your proposed sequence. CH3H3CCH3BrH3CHCH3H3CH3COHt-BuOK/t-butanolCH3H3CH3C1-BH32-H2O2, OHMulti-step Synthesis CH2OHCH31) NaH2)CH2BrCH3H3CH2COCH3CH3H3C(1) Hg(O2CCH3)2, H2O(2) NaBH4, NaOHOHH3CCl ClCH3H3C CH31) NaNH2, 3 equivalentsBrH3CC2H5H2)3) Pt, H2 (1 mole)H(H3C)3CHH3CC2H5HMulti-step SynthesisC9H10O2 MS IR 1HNMR 13CNMR 1H 5H 2H 2H CO2HHBrC2H5O-, C2H5OH(1) OsO4, Pyridine(2) NaHSO3, H2O(1) KMnO4, OH-, heat(2) H3O+O+CO2 +