1. Trang chủ
  2. » Khoa Học Tự Nhiên

Bài giảng hóa hữu cơ phản ứng của arene

13 317 0

Đang tải... (xem toàn văn)

Tài liệu hạn chế xem trước, để xem đầy đủ mời bạn chọn Tải xuống

THÔNG TIN TÀI LIỆU

Thông tin cơ bản

Định dạng
Số trang 13
Dung lượng 22,9 KB

Nội dung

Some reactions involve the ring.. In other reactions the ring is a substituent... a ReductionCatalytic hydrogenation Section 11.4 Birch reduction Section 11.11 b Electrophilic aromatic s

Trang 1

11.10 Reactions of Arenes:

A Preview

1 Some reactions involve the ring

2 In other reactions the ring is a substituent

Trang 2

a) Reduction

Catalytic hydrogenation (Section 11.4) Birch reduction (Section 11.11)

b) Electrophilic aromatic substitution

(Chapter 12) c) Nucleophilic aromatic substitution

(Chapter 23)

1 Reactions involving the ring

2 The ring as a substituent (Sections 11.12-11.17)

Trang 3

catalytic

hydrogenation

(Section 11.4)

Birch reduction (Section 11.11) H

H

H H

H

H

Reduction of Benzene Rings

H H

H

H

H

H H

H

Trang 4

11.11 The Birch Reduction

Trang 5

H

H

H H

H

H

Na, NH3

CH3OH

Birch Reduction of Benzene

Product is non-conjugated diene.

Reaction stops here There is no further reduction.

Trang 6

H

H H

Step 1: Electron transfer from sodium

Mechanism of the Birch Reduction (Figure 11.8)

H

H

H

H

H

H

••

Trang 7

Step 2: Proton transfer from methanol

Mechanism of the Birch Reduction (Figure 11.8)

H

H

H

H

H

H

••

OCH3

H

••

Trang 8

Step 2: Proton transfer from methanol

Mechanism of the Birch Reduction (Figure 11.8)

H

H

H

H

H

H

••

OCH3

H

••

H

H

H

H

H H

H

OCH3

••

• ••

Trang 9

Step 3: Electron transfer from sodium

Mechanism of the Birch Reduction (Figure 11.8)

H

H

H

H

H H

H

+ •Na

Trang 10

Step 3: Electron transfer from sodium

Mechanism of the Birch Reduction (Figure 11.8)

H

H

H

H

H H

H

+ •Na

H

H

H

H

H H

H

••

+ Na+ –

Trang 11

Step 4: Proton transfer from methanol

Mechanism of the Birch Reduction (Figure 11.8)

H

H

H

H

H H

H

••

• OCH3 H

••

Trang 12

Step 4: Proton transfer from methanol

Mechanism of the Birch Reduction (Figure 11.8)

H

H

H

H

H H

H

••

• OCH3 H

••

H

H

• OCH3

••

••

Trang 13

H

H

H H

H

H

Na, NH3

CH3OH

Birch Reduction of an Alkylbenzene

If an alkyl group is present on the ring, it ends up as

a substituent on the double bond

Ngày đăng: 01/06/2015, 19:36

TỪ KHÓA LIÊN QUAN

w