Ktl-icon-tai-lieu

chapter 11

Được đăng lên bởi hakate-senpai
Số trang: 42 trang   |   Lượt xem: 1146 lần   |   Lượt tải: 0 lần
ORGANIC CHEMISTRY
Dr Nam T. S. Phan
Faculty of Chemical Engineering
HCMC University of Technology
Office: room 211, B2 Building
Phone: 38647256 ext. 5681
Email: ptsnam@hcmut.edu.vn
1

Chapter 11:
C=O

ALDEHYDES-KETONES
C=C

SP2 carbon
2

NOMENCLATURE OF ALDEHYDES
Common names: carboxylic acid Æ “aldehyde”
is substituted for “ic acid”

IUPAC names: hydrocarbon + al

3

Lower priority than ester Æ “oxo” group

4

5

NOMENCLATURE OF KETONES
Derived names: alkyls + ketone

IUPAC names: hydrocarbon + one

6

7

PREPARATION OF ALDEHYDES &
KETONES

Aldehydes & ketones from alkenes

In the presence of an oxidizing agent, the products
8
will be ketones / carboxylic acids

Aldehydes & ketones from alkynes
Markovnikov’s rule

Anti-Markovnikov
9

Aldehydes & ketones from alcohols

10

Can NOT be isolated

PCC: pyridinium chlorochromate
11

Aldehydes from esters, acyl chlorides

Note: LiAlH4 Æ alcohols

12

Preparation of aromatic ketones

13

Gatterman-Koch synthesis of benzaldehyde

Can NOT be
prepared &
isolated
14

REACTIONS OF ALDEHYDES &
KETONES I

The partial positive
carbon can be attacked
by nucleophiles

The addition of nucleophiles to the carbon
atom of the carbonyl group in nucleophilic
addition reactions
15

Reactions with Grignard reagents

Only for the reaction of HCHO
16

Numbers 1 & 2 are used to indicate that the acid is not added
until the reaction with the Grignard reagent is complete

17

Reactions with acetylide ions

Weak acid, will NOT react with the triple bond

18

Reactions with hydrogen cyanide

Converted back to carbonyl in basic solutions

19

Nitriles Æ carboxylic acids

Nitriles Æ amines

20

Reactions with primary amines

21

Reaction mechanism:

22

Reactions with secondary amines

23

Reaction mechanism:

24

Reactions with water

25

Reactions with alcohols

26

Reaction mechanism:

27

Reactions with sulfur nucleophiles

28

Reduction reactions – with hydride ion

29

• NaBH4 can reduce aldehyde, ketones, acyl chlorides, but
NOT alkenes & alkynes
• LiAlH4 is a stronger reducing agent than NaBH4, but NOT
safe to use for aldehydes & ketones

30

Reduction reactions to hydrocarbons

NOTE:

31

Oxidation reactions

Aldehydes are generally easier to oxidize than
primary alcohols

32

Tollens reagent

Too weak to oxidize an
alcohol or any other
functional groups
Should be used when oxidizing aldehydes
containing double bond

33

REACTIONS OF ALDEHYDES &
KETONES II – REATIONS AT α-C

34

Aldol additions

3...
1
ORGANIC CHEMISTRY
Dr Nam T. S. Phan
Faculty of Chemical Engineering
HCMC University of Technology
Office: room 211, B2 Building
Phone: 38647256 ext. 5681
Email: ptsnam@hcmut.edu.vn
chapter 11 - Trang 2
Để xem tài liệu đầy đủ. Xin vui lòng
chapter 11 - Người đăng: hakate-senpai
5 Tài liệu rất hay! Được đăng lên bởi - 1 giờ trước Đúng là cái mình đang tìm. Rất hay và bổ ích. Cảm ơn bạn!
42 Vietnamese
chapter 11 9 10 170