aldehyde, ketone, carbonyl group, nucleophilic addition, aldol condensation.

aldehyde ketoneHCHOHRR

C=O C=O

:3--3-2,4,5--3--methyl-3-butenal2,4,5-trimethyl-3-hexanonephenylmethanalacetophenone

carbonyl group HCHOC Osp2COp O > COsp2sp2-sp2

C=OIR 1690~1760 cm-1C=O 2700~2850 cm-1O=C-H1HNMR 9~10 ppm-CHO 2~3 ppm-CH2-CHO

nucleophilic addition C=OR+IC+

1. HCN8COH-[CN-]C

2. R-OHH2O OH-H+

H2O-I

3. GrignardR-MgX+-

2--2-

4.2,4-

a- p-

1. aldol condensation-H

2. -HOH-I2/NaOHCHI3

10-7P192

1. TollensFehling

2. [H](1) H2/NiPtC=CC=O

(2) LiAlH4NaBH4C=OC=C(3) Zn-Hg/HClClemmensenC=OCH2

HCNROHH2OGrignardH2N-G2,4- TollensFehlingH2/NiLiAlH4orNaBH4Zn-Hg/HCl C=O 1. 2. H 3.

P197 3(), 8, 9/(1)(3), 12, 13/(1)(3) P16If we takethe same carbon atom P17 Aldol reaction 2- 3-I2/NaOH2,4-TollensFehling Ag Ag Ag