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403221 เคมีอินทรีย์ แอล ดีไฮด์ และ คีโตน. ผศ. ดร. วราภรณ์ พาราสุข ภาควิชาเคมี คณะวิทยาศาสตร์ มหาวิทยาลัยเกษตรศาสตร์. โครงสร้าง. หมู่คาร์บอนิล C=O สูตรทั่วไป C n H 2n O. การเรียกชื่อแอลดีไฮด์ (aldehyde). ชื่อสามัญ - PowerPoint PPT Presentation
403221 . .
403221-aldehyde
C=O CnH2nO
403221-aldehyde
(aldehyde) -(o)ic acid aldehyde
403221-aldehyde
IUPAC alkanal 1
403221-aldehyde
(ketone)
403221-aldehyde
2 C=O ketone
403221-aldehyde
IUPAC alkanone
403221-aldehyde
403221-aldehyde
MW (oC)
CH3CH2CH2-C-H72 76CH3CH2-C-CH372 80CH3CH2CH2CH2CH372 36CH3CH2OCH2CH374 35CH3CH2CH2CH2OH74118
403221-aldehyde
C=O dipole
403221-aldehyde
403221-aldehyde
1. oxidation 1o ROH C
403221-aldehyde
2. Reimer-Tiemann reaction phenolic aldehyde
3. Gatterman-Koch reaction aromatic aldehyde
403221-aldehyde
4. Rosenmund reduction
403221-aldehyde
1. oxidation 2o ROH
403221-aldehyde
2. hydration alkyne
403221-aldehyde
3. hydrolysis geminal dihalide
403221-aldehyde
4. Friedel-Craft acylation C
403221-aldehyde
5. nitrile RMgX RLi C
403221-aldehyde
6. acid chloride R2CuLi C R, R alkyl aryl
403221-aldehyde
403221-aldehyde
7. acid chloride organocadmium C
403221-aldehyde
Grignard reagent organolithium organocadmium
403221-aldehyde
8. ozonolysis alkeneAsymmetric alkene 2 Symmetric alkene
403221-aldehyde
1. nucleophilic additionNucleophile HCNhydrogen cyanideROH alcoholNaHSO3sodium bisulfiteRMgXGrignard reagentHNH2ammonia ammonia
403221-aldehyde
1.1. Addition of HCN
403221-aldehyde
403221-aldehyde
1.2. Addition of alcohol
403221-aldehyde
403221-aldehyde
403221-aldehyde
403221-aldehyde
1.3. Addition of bisulfite aldehyde ketone
403221-aldehyde
1.4. Addition of Grignard reagent (RMgX)
403221-aldehyde
403221-aldehyde
1.5. Addition of ammonia derivativeReagentProduct
NH2OHhydroxylamineoxime
NH2NH2hydrazinehydrazone
phenylhydrazinephenylhydrazone
semicarbazidesemicarbazone
403221-aldehyde
403221-aldehyde
2. Oxidation2.1. Oxidation of aldehyde aldehyde ketone
403221-aldehyde
Fehlings reagent = Cu2+ tartrate complexBenedicts reagent= Cu2+ citrate complex aliphatic aromatic aldehyde
403221-aldehyde
2.2. Oxidation of methyl ketone (iodoform test)alcohol oxidize methyl ketone haloform
403221-aldehyde
3. Reduction3.1. Reduction to alcohol
403221-aldehyde
3.2. Reduction to hydrocarbon
403221-aldehyde
4. a-hydrogen4.1. Keto-enol tautomerization Enolate anion Resonance resonance form
403221-aldehyde
4.2. Halogenation a-H
403221-aldehyde
iodoform
403221-aldehyde
403221-aldehyde
4.3. Aldol condensation
403221-aldehyde
aldol dehydration
403221-aldehyde
5. Canizzaro reaction aldehyde a-Hautooxidation-reduction
403221-aldehyde
403221-aldehyde