????????????? C=O

1
403221 ?????????????????????????????

• ??. ??. ??????? ???????
• ??????????? ??????????????
• ??????????????????????

2
?????????

• ????????????? CO
• ?????????? CnH2nO

3
????????????????????? (aldehyde)

• ?????????
• ??????????????????????????????????????????????????
  ??????????? -(o)ic acid ???? aldehyde

4

• ???? IUPAC
• ???????????????????????????????
  ?????????????????? alkanal ???????
  ?????????????? 1

5
????????????????? (ketone)

• ?????????
• ??????????????????

6

• ?????????????????? 2 ????????????????? CO
  ????????????????????????? ketone

7

• ???? IUPAC
• ???????????????????????????????
  ?????????????????? alkanone ??????????????????
  ???????????????????????

8
(No Transcript)
9
???????????????

• ????????
• MW ???????? (oC)
• CH3CH2CH2-C-H 72 76
• CH3CH2-C-CH3 72 80
• CH3CH2CH2CH2CH3 72 36
• CH3CH2OCH2CH3 74 35
• CH3CH2CH2CH2OH 74 118

10

• ????????? ???????????????????????????? ??????????
  ??????????????????????????????????????????????
• ?????????????????? CO ?????????????? ??????????
  dipole ????????????????????????
  ???????????????????????????????????

11

• ????????
• ????????? ????????????????????????????????????????
  ??????????????????????
• ???????????????????????????????

12
??????????????????

• 1. ????????? oxidation ??? 1o ROH

?????????????????????? C ?????????????????
13

• 2. Reimer-Tiemann reaction ????????????? phenolic
  aldehyde

3. Gatterman-Koch reaction ?????????????
aromatic aldehyde
14
4. Rosenmund reduction
15
??????????????

• 1. ????????? oxidation ??? 2o ROH

16

• 2. ????????? hydration ??? alkyne

17

• 3. ????????? hydrolysis ??? geminal dihalide

18

• 4. ????????? Friedel-Craft acylation

?????????????????? C ?????????????????
19

• 5. ???????????????? nitrile ??? RMgX ???? RLi

?????????????????? C ?????????????????
20

• 6. ???????????????? acid chloride ??? R2CuLi

R, R ??????? alkyl ???? aryl ?????
?????????????????? C ?????????????????
21
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22

• 7. ???????????????? acid chloride ???
  organocadmium

?????????????????? C ?????????????????
23

• ?????? Grignard reagent ???? organolithium ???
  organocadmium

24

• 8. ????????? ozonolysis ??? alkene

Asymmetric alkene ???????????? 2 ???? Symmetric
alkene ?????????????????????
25
??????????????????????????????1. nucleophilic
addition
Nucleophile ?????? HCN hydrogen cyanide ROH
alcohol NaHSO3 sodium bisulfite RMgX Grignard
reagent HNH2 ammonia ??? ??????????? ammonia
26

• 1.1. Addition of HCN

27
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28

• 1.2. Addition of alcohol

29
(No Transcript)
30

• ?????????????

31
(No Transcript)
32

• 1.3. Addition of bisulfite

?????? aldehyde ketone ???????????????????????????
33

• 1.4. Addition of Grignard reagent (RMgX)

34
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35

• 1.5. Addition of ammonia derivative

Reagent Product NH2OH hydroxylamine oxime
NH2NH2 hydrazine hydrazone phenylhydrazin
e phenylhydrazone semicarbazide semicarb
azone
36

• ?????????????

37
2. Oxidation

• 2.1. Oxidation of aldehyde
• ???????????????????????? aldehyde ??? ketone

38
Fehlings reagent Cu2 tartrate
complex Benedicts reagent Cu2 citrate
complex ???????????????????????? aliphatic ???
aromatic aldehyde
39

• 2.2. Oxidation of methyl ketone (iodoform test)

alcohol ??? oxidize ??????? methyl ketone ??????
haloform ???????
40
3. Reduction

• 3.1. Reduction to alcohol

41

• 3.2. Reduction to hydrocarbon

42
4. ???????????? a-hydrogen

• 4.1. Keto-enol tautomerization

Enolate anion ????????????? Resonance
resonance form
43

• 4.2. Halogenation ?????????????????????? a-H

?????????????
44

• ??????? iodoform

45
?????????????
46

• 4.3. Aldol condensation

?????????????
47
???????????????? aldol ?????? dehydration
48
5. Canizzaro reaction

• ?????????????? aldehyde ???????? a-H
• autooxidation-reduction

49
?????????????