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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