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Oxidation of alcohols

Oxidation of alcohols. 1+. 2-. 2-. 1+. 2-. 3+. 1-. 1+. 1+. 1+. 1+. 2-. carboxylic acid. aldehyde. 1 o alcohol. [O] = oxidizing agent. Cr 2 O 7 2-. dichromate. Cr 3+. permanganate. MnO 4 -. weak oxidizing agent. 1 o alcohol  aldehyde. PCC. 1. binding O

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Oxidation of alcohols

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  1. Oxidation of alcohols 1+ 2- 2- 1+ 2- 3+ 1- 1+ 1+ 1+ 1+ 2- carboxylic acid aldehyde 1o alcohol [O] = oxidizing agent Cr2O72- dichromate Cr3+ permanganate MnO4- weak oxidizing agent 1o alcohol  aldehyde PCC 1. binding O 2. removing H oxidation = lossof e- densityfrom C

  2. Alcohols oxidation of alcohols: [O] = Cr2O72- or MnO42- [O] [O] aldehyde carboxylic acid 1o alcohols [O] [O] + Cr3+ + Cr2O72- methanal methanol methanoic acid formaldehyde formic acid

  3. Alcohols oxidation of alcohols: [O] = Cr2O72- or MnO42- or PCC [O] [O] ketone no reaction 2o alcohols [O]

  4. Alcohols oxidation of alcohols: [O] = Cr2O72- or MnO42- or PCC [O] no reaction 3o alcohols

  5. Aldehydes and Ketones 120o ketone aldehyde C=O carbonyl group C and O are sp2 hybridized

  6. Aldehydes and Ketones Nomenclature 1. Longest chain with C=O is parent 2. Suffix is “-al” or “-one” 3. C1 is always C=O in aldehydes In ketones, C=O is given lowest number 4. C=O has precedence over -OH (called “hydroxy”)

  7. 2-bromo-3-methyl butan al 3 4 2 1 pentan one 3- 1 4 2 5 3 trans- 1 3-hydroxy- 2 2-methyl cyclobutanone 3

  8. - H .. : O C .. H H .. + C O .. H Physical properties + - polar higher b.p. than alkanes H-bond acceptor soluble in polar solvents lower b.p. than alcohols no H-bond donor

  9. Reactions Reduction [R] = reducing agent LiAlH4 NaBH4 H2/Pt [R] 4 3 1 2 CH3- CH3- CH2- CH2- CH2- CHO CH2- CH2- OH butan al [R] 1 3 4 2 2- butan one

  10. Reactions Reduction: LiAlH4 H2/ Pt NaBH4

  11. Alkanes CnH2n+2 conformations (Newman) optical isomers LDF CnH2n cyclic geometric isomers combustion halogenation

  12. Alkyl halides Nucleophilic substitution SN2 1o transition state inversion of stereocenter SN1 3o carbocation racemic mixture 2o ?

  13. Alkenes sp2 CnH2n geometric isomers Addition reactions H – X H – OH H – H Br – Br polymerization

  14. Alcohols CnH2n+2O H-bonding dehydrate most substituted alkene oxidize 1o aldehyde carboxylic acid 2o ketone 3o no reaction condensation 2 alcohol  ether + water

  15. reduction aldehyde CnH2nO  1o alcohol H2/Pt, NaBH4, LiAlH4 CnH2nO ketone  2o alcohol H2/Pt, NaBH4, LiAlH4 carboxylic acid CnH2nO2  1o alcohol only LiAlH4

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