Slide Bài tập CARBONYL

Aldehydes feature an sp2hybridized, planar carbon center that is connected by a double bond to oxygen and a single bond to hydrogen. The CH bond is not acidic. Because of resonance stabilization of the conjugate base, an αhydrogen in an aldehyde (not shown in the picture above) is far more acidic, with a pKa near 17, than a CH bond in a typical alkane (pKa about 50).2 This acidification is attributed to (i) the electronwithdrawing quality of the formyl center and (ii) the fact that the conjugate base, an enolate anion, delocalizes its negative charge. Related to (i), the aldehyde group is somewhat polar. Aldehydes (except those without an alpha carbon, or without protons on the alpha carbon, such as formaldehyde and benzaldehyde) can exist in either the keto or the enol tautomer. Ketoenol tautomerism is catalyzed by either acid or base. Usually the enol is the minority tautomer, but it is more reactive.

ALDEHYD VÀ CETON BÉO

Propenal Acrolein Crotonaldehyd but-2-en-1-al

Ethandial Glyoxal

5-methylhex-4-en-2-on Methylvinylceton 3-phenylpropanal

pentan-2,4-dion

acetoaceton 1,1-dimethoxyethan

3-oxobutanal Acetoacetandehyd

2,6-di (4’-hydroxy-3’-methoxybenzyl) cyclohexanol

3 Aldol hóa:

a.

b.

c Propen  propanal

d Cyclohexen  cyclohexanon:

4.

5 Điều chế butanon:

a Từ 2-chlorobutan

b T ethanal ừ

c Từ 2,3-dichlorobutan

5.

d Từ acetonitril

6 Điều chế aceton từ

a Ethanol:

b Từ propanol:

c Từ acetylen

i.

k.

7.

d.

natributynylid

8

9 Phân biệt:

a .

b.

10 Điều chế pentaerythritol Gọi tên theo IUPAC

2,2-di(hydroxymethyl)propan-1,3-diol

Tetrahydroxyneopentan

ALDEHYD VÀ CETON THƠM

acetophenon phenylvinylceton

ethyl-p-methoxyphenylceton acetophenoxim

methylphenylcetoxim

Di-(p-dimethylaminophenyl)ceton

9,10-formylanthracen Anthracen-9,10-dicarbaldehyd

Anthraquinon Anthracen-9,10-dion

2-formylthiophen Thiophen-2-carbaldehyd

Di(p-tolyl)ceton

p,p’-dimethylbenzophenon

2 Viết công thức:

phenyl-p-tolylceton o-chlorobenzaldehyd p-nitrobenzaldehyd

acetophenon 4,4’-dibromobenzophenon p-dimethylaminobenzaldehyd

4.Viết p/ứ :

Cyanohydrin-p-tolylaldehyd

Bisulfitic p-tolylaldehyd

N-phenyl-p-tolualdimin

5 Phân biệt

a Acetaldehyd và benzaldehyd: p/ứ haloform

b p-tolylaldehyd và acetophenon: -p/ứ haloform

-tt Schiff, Tollens, Fehling

7 Từ benzen đ/c p-clorobenzaldehyd Viết p/ứ ngưng tụ với propionaldehyd,

methylethylceton, annhydrid acetic

9.Thực hiện chuyển hóa:

a.

b.

c.

e.

10 Từ benzen đ/c vanilin qua g/đ tạo gaiacol:

vanilin

gaiacol

P/ứ ngưng tụ giữa vanilin và anilin:

11 Hoàn thành qui trình điều chế

a Bisacodyl: nhuận tràng

(A)

b Các vitamin K:

11.

c Haloperidol: an thần

11.

d Progabid: trị động kinh

e Amfepramon: thuốc gây chán ăn

11.

Miconazol

h.

11.

13 Tổng hợp amiodaron:

HBr