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Lecture18 2
Lecture18 2
Lecture
Ketones and Aldehydes
Classes of Carbonyl
Compounds
Chapter 18
Chapter 18
Resonance
Chapter 18
Ketone Nomenclature
Chapter 18
Chapter 18
Boiling Points
Chapter 18
Chapter 18
Formaldehyde
Chapter 18
Chapter 18
10
IR Spectra
Chapter 18
11
Chapter 18
12
H NMR Spectroscopy
Chapter 18
13
Chapter 18
14
McLafferty Rearrangement
Chapter 18
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Chapter 18
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Chapter 18
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Chapter 18
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Chapter 18
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Chapter 18
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Chapter 18
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Ozonolysis of Alkenes
Chapter 18
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FriedelCrafts Reaction
Chapter 18
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Hydration of Alkynes
Chapter 18
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HydroborationOxidation of
Alkynes
Chapter 18
25
Solved Problem 1
Showhowyouwouldsynthesizeeachcompoundfromstartingmaterialscontainingnomorethansix
carbonatoms.
(a)
(b)
Solution
(a) Thiscompoundisaketonewith12carbonatoms.Thecarbonskeletonmightbeassembledfrom
twosixcarbonfragmentsusingaGrignardreaction,whichgivesanalcoholthatiseasilyoxidized
tothetargetcompound.
Chapter 18
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(b) Thiscompoundisanaldehydewitheightcarbonatoms.Analdehydemightcomefromoxidation
ofanalcohol(possiblyaGrignardproduct)orhydroborationofanalkyne.IfweuseaGrignard,
therestrictiontosixcarbonstartingmaterialsmeansweneedtoaddtwocarbonstoa
methylcyclopentylfragment,endinginaprimaryalcohol.Grignardadditiontoanepoxidedoes
this.
Chapter 18
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Chapter 18
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Chapter 18
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Chapter 18
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Reduction of Nitriles to
Aldehydes
Chapter 18
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Chapter 18
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Chapter 18
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Nucleophilic Addition
Chapter 18
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Chapter 18
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Chapter 18
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Oxaphosphetane formation
Chapter 18
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Chapter 18
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Chapter 18
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Solved Problem 2
ShowhowyouwoulduseaWittigreactiontosynthesize1phenyl1,3butadiene.
Chapter 18
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Youshouldcompletethissolutionbydrawingoutthesynthesesindicatedbythisanalysis
(Problem1816).
2013 Pearson Education, Inc.
Chapter 18
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Chapter 18
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Acid-Catalyzed Hydration of
Carbonyls
Chapter 18
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Base-Catalyzed Hydration of
Carbonyls
Chapter 18
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Cyanohydrin Formation
Chapter 18
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Formation of Imines
Chapter 18
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Acid-catalyzed dehydration
Chapter 18
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Chapter 18
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Chapter 18
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Formation of Acetals
Chapter 18
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Must be acid-catalyzed.
Adding H+ to carbonyl makes it more reactive
with weak nucleophile, ROH.
2013 Pearson Education, Inc.
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Acetal Formation
Chapter 18
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Hydrolysis of Acetals
Chapter 18
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Cyclic Acetals
Chapter 18
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HO
OH
Chapter 18
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Chapter 18
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O
H
O
1) NaBH4
2) H3O+
H
OH
Chapter 18
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Oxidation of Aldehydes
Chapter 18
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Chapter 18
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Reduction Reagents
Sodium borohydride, NaBH4, can reduce
ketones to secondary alcohols and aldehydes
to primary alcohols.
Lithium aluminum hydride, LiAlH4, is a
powerful reducing agent, so it can also
reduce carboxylic acids and their derivatives.
Hydrogenation with a catalyst can reduce the
carbonyl, but it will also reduce any double or
triple bonds present in the molecule.
2013 Pearson Education, Inc.
Chapter 18
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Sodium Borohydride
Chapter 18
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O
R
R(H)
LiAlH4
ether
R(H)
aldehyde or ketone
Chapter 18
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Catalytic Hydrogenation
Chapter 18
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Chapter 18
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Clemmensen Reduction
Chapter 18
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