ไม่มีชื่อเรื่องภาพนิ่ง

ไม่มีชื่อเรื่องภาพนิ่ง

403221 . . 403221-aldehyde 1 C=O CnH2nO p-orbital sp2-C C O ~120o

~120o sp2-O O H C H formaldehyde O R C H aldehyde 403221-aldehyde C + O O

R C R' ketone 2 C R H (aldehyde)aldehyde) O -(o)ic o)ic ic acid ald ehyde O H

O O C C H formaldehyde H3C C H H acetaldehyde

403221-aldehyde benzaldehyde 3 IUPAC alkanal 1 O C O

C H H H O O C C H3C H ethanal H

methanal O O H2C C H C propenal H CH3CH2CH2 CH C H CH3 2-methylpentanal 403221-aldehyde 4

O C R R' (aldehyde)ketone) O C H3C CH3 acetone O O

C C CH3 acetophenone 403221-aldehyde benzophenone 5 2 C=O ketone H3C O

O C C H3C CH2CH3 ethyl methyl ketone CH2 benzyl methyl ketone 403221-aldehyde 6

IUPAC alkanone O C O C O O H3C

C H3C CH2CH3 butanone CH3CH2 O C C CH2 H3C CH3

propanone phenylpropanone O O C C CH2CH3 3-pentanone H3C CH2CH2CH3 2-pentanone 403221-aldehyde

7 O cyclic ketone C H3C 1 O 4-methylcyclohexanone O 4-methyl-3-penten-2-one 403221-aldehyde

8 (o)ic C)ic o MW O CH3CH2CH2-C-H O 72 76 CH3CH2-C-CH3

72 80 CH3CH2CH2CH2CH3 72 36 CH3CH2OCH2CH3 74 35 CH3CH2CH2CH2OH 74

118 403221-aldehyde 9 C=O dipole 403221-aldehyde 10

.. :O H .. :O C H .. :O C 403221-aldehyde 11

1. oxidation 1o ROH NH + O H R C H H 1o alcohol CuO PCC O R C H NCrO3HCl

PCC aldehyde CH3(o)ic CH2)ic 4 CH2OH CH3 CH2OH PCC CuO, CrO3Cl O CH3(o)ic CH2)ic 4 C H O CH3 C H C 403221-aldehyde

12 2. Reimer-Tiemann reaction phenolic aldehyde 3. Gatterman-Koch reaction aromatic aldehyde O AlCl , Cu Cl + CO + HCl 3

2 2 403221-aldehyde C H 13 4. Rosenmund reduction O R C Cl H2, Pd/ BaSO4 solvent O R C H

403221-aldehyde 14 1. oxidation 2o ROH 403221-aldehyde 15 2. hydration alkyne 403221-aldehyde 16 3. hydrolysis geminal dihalide

403221-aldehyde 17 4. Friedel-Craft acylation C 403221-aldehyde 18 5. nitrile RMgX RLi H2O, H+ + + ether R

R C N MgX R C N + R'-MgX O C R' R' + R C N + + R'-Li ether

R C N Li H2O, H+ O R C R' R' 403221-aldehyde C 19 6. acid chloride R2CuLi R2CuLi

+ CuX O O R' C Cl R' C R RLi Li RX R, R alkyl aryl

C 403221-aldehyde 20 403221-aldehyde 21 7. acid chloride organocadmium O O R' C Cl R2Cd or RCdCl R' C R

403221-aldehyde C 22 Grignard reagent organolithium organocadmium 403221-aldehyde 23 8. ozonolysis alkene R R' C C

R'' H O 1)ic O3 2)ic Zn, H2O R' C H O + R'' C R Asymmetric alkene 2 403221-aldehyde Symmetric alkene 24

1. nucleophilic addition Nucleophile HCN hydrogen cyanide ROH alcohol NaHSO3 sodium bisulfite RMgX Grignard reagent HNH2 ammonia ammonia 403221-aldehyde 25 1.1. Addition of HCN 403221-aldehyde

26 403221-aldehyde 27 1.2. Addition of alcohol 403221-aldehyde 28 403221-aldehyde 29 403221-aldehyde 30

403221-aldehyde 31 1.3. Addition of bisulfite aldehyde ketone 403221-aldehyde 32 1.4. Addition of Grignard reagent (aldehyde)RMgX) + C O

+ + R-MgX ether C O MgX H2O,H+ R R H C O H R

C O H R C O R' 1)ic R-MgX, ether 2)ic H2O,H+ 1)ic R-MgX, ether C O H R CH2 O H 1o alcohol R R CH O H 2o alcohol

2)ic H2O,H+ 1)ic R-MgX, ether 2)ic H2O,H+ R R C O H 3o alcohol R' 403221-aldehyde 33 403221-aldehyde 34

1.5. Addition of ammonia derivative Reagent Product NH2OH hydroxylamine oxime NH2NH2 hydrazine hydrazone phenylhydrazine phenylhydrazone semicarbazide

semicarbazone 403221-aldehyde 35 403221-aldehyde 36 2. Oxidation 2.1. Oxidation of aldehyde aldehyde ketone 403221-aldehyde

37 Fehlings reagent = Cu2+ tartrate complex Benedicts reagent = Cu2+ citrate complex aliphatic aromatic aldehyde 403221-aldehyde 38 2.2. Oxidation of methyl ketone (aldehyde)iodoform test) alcohol oxidize methyl ketone haloform 403221-aldehyde 39

3. Reduction 3.1. Reduction to alcohol 403221-aldehyde 40 3.2. Reduction to hydrocarbon 403221-aldehyde 41 4. C-C hydrogen O

C C C C C H-H 4.1. Keto-enol tautomerization Enolate anion resonance form 403221-aldehyde 42 4.2. Halogenation -H

403221-aldehyde 43 iodoform 403221-aldehyde 44 O CH3CH2 C C H H2 OH CH3CH2 C C I H OH-

OH- O I CH3CH2 C C I H O CH3CH2 C C I 3 OH- O CH3CH2 C CH2 O CH3CH2 C C I H O I CH3CH2 C C I I

I I O I I CH3CH2 C C I H I O OH- O CH3CH2 C C I 3 OH 403221-aldehyde CH3CH2 C C I

H2 O I I CH3CH2 C C I I O CH3CH2 C OH + C I 3 O CH3CH2 C O + CH I 3 45 4.3. Aldol condensation

403221-aldehyde 46 aldol dehydration O H OH O H OH H C C C CH3 H H OH- H C C- C CH3 H 403221-aldehyde O H

H C C C CH3 H crotonaldehyde -unsaturated carbonyl 47 5. Canizzaro reaction aldehyde -H autooxidation-reduction 403221-aldehyde 48 403221-aldehyde 49

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