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有机化学. 主讲教师 霍文兰 教 材 曾昭琼 主编. 第十一章 醛和酮. Chapter 11 Aldehyde and Ketone. 目的与要求. 要求学生掌握亲核加成反应的基本概念、反应类型和反应机理,醛和酮的基本化学性质和制备方法;了解影响亲核加成反应的各种因素, α,β 不饱和羰基化合物的性质等。. 教学重点和难点. 重点 1. 亲核加成反应:反应机理、立体化学等 2. 醛和酮的其它化学性质:卤仿反应、羟醛缩合反应、氧化还原反应、共轭加成反应等 难点 亲核加成反应的立体化学、羟醛缩合反应等. 本章提纲.

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Chapter 11

Aldehyde and Ketone


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,


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1.

2.


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CH3CH2CHO

CH3COCH3


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  • 1

  • ealone

3-

3-

3-methylbutanal

3-pentanone


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2-

2-phenylpropanal

4-formylbenzoic acid

3-

3-hydroxylbutanal


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3-()

1,2-

3-methylcyclopentadcanone

1,2-naphthalene dicarbaldehyde

2--1--1-

1-cyclohexyl-2-methyl-1-propanone


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CH3CHO

CH3COCH3

acetaldehyde

acetone


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sp2

sp22p

2p2p


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  • sp2120120

  • -

121.5

117


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40%

11


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  • C=O1750~1680cm-1(1730cm-1)(1715cm-1)

  • CH2750 cm-1


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1727 cm-1C=O2846 cm-12733 cm-1CH

3001 cm-1CH1350 cm-1CH


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1686 cm-1C=O

1559~1450 cm-13060~3010 cm-1CH


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  • ()10

  • 2.0~2.5


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d.

a.

b.

c.

d

b

a

c

CH3CH2CH2CHO


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c.

a.

b.


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-


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(1)

  • 7HCN-

HCN

  • HCN


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  • -

-


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Grignard


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(2)

  • -1

  • -C


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  • HCl


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  • H+


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  • 8NaHSO3-NaHSO3


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(3)


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()


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  • HSchiff

Schiff


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  • H-H

  • Np--


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  • pH = 5


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(Z)-

(E)-


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(4) Wittig

  • (ylide)


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-

  • -

  • --p-


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(1)-

  • -

20%

80%

100%

0%


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(2)


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2-


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(3)

  • --,-


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--


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-

--


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---


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(1)

lindlar


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  • LiAlH4NaBH4


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  • Meerwein-Ponndorf-Verley

Oppenauer


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-Wolff -

Clemmensen


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(2)

Tollens

Ag2O


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Fehling


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  • Baeyer-Villiger


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(3)

  • -Cannizzaro


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  • Cannizzaro


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  • (Schiff)SO2


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  • HCNCN

  • HCNKC10-3~103HCN


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KC = 38

KC << 1


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KC = 210

KC = 530


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KC = 210

KC > 104


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KC > 104

KC = 1.06


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-

  • pH5


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Nu-


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(1)

86%

14%


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(2)

  • Cram

MS

S


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75%

25%


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(3)

LiAlH4

90%

10%

LiBH(s-Bu)3

12%

88%


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  • C = CCHCrO3SeO2


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bp. 92.7

bp. 49


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Friedel-Crafts


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  • Gattermann-Koch

  • Vilsmeier-Haack


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  • Rosenmund


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  • Grignard

GrignardCdCl2


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  • CH2(OH)2


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  • Beckmann

  • Beckmann


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,-


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  • H2OROHRCOOHHXNH3


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  • Grignard


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,-

(1)

  • ,-


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(2)

  • HCNNaHSO3ROH1,4-


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  • Grignard1,2-1,4-1,4-


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(3) Michael

  • ,-,-


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  • Robinson


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(4)

  • ,-Diels-Alder


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(5)

  • -

2-


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  • ,-


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  • 2--1,4-


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