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有机化学第十四章

有机化学第十四章

COOC2H5 CH3COCH2COOC2H5 + C2H5OH COCH2COOC2H5
两种产物在性质上有较大差别， 两种产物在性质上有较大差别，可分离
分子内Claisen 酯缩合（Dieckmann狄克曼缩合） 酯缩合（ 狄克曼缩合） 分子内 狄克曼缩合
CH2CH2COOC2H5 CH2CH2COOC2H5 O
C2H5C O + CH2COOC2H5 CN CH3
乙酸铵－乙酸
C6H6
CH3 C2H5
C C COOC2H5 CN 85%
CHO
+
CH2(COOH)2
哌啶,95~100℃ ℃ -H2O
CH C(COOH)2
- CO2
CH CHCOOH (80%~95%)
五、Michael加成 加成
O + CH2(COOC2H5)2 C2H5ONa C2H5OH CH(COOC2H5)2 90% (C2H5)3N,叔丁醇 叔 O
三、丙二酸二乙酯的合成及应用
1、制备 、
CH2COONa Cl
NaCN
CH2COONa CNOC H 2 5
腈化反应
水解、 水解、成酯反应
2、应用 、 （1）制备取代乙酸（一取代或二取代）： ）制备取代乙酸（一取代或二取代）： 脱H+,生成钠盐 生成钠盐
步2
制备甲基酮或烷基取代酸： 制备甲基酮或烷基取代酸：
①稀OH -,②H+,③∆ 酮式分 解 ①40%OH-,②H+,③∆ 酸式分解
CH3 CH3COCCOOC2H5 CH2CH2CH3
CH3 CH3COCHCH2CH2CH3
CH3 CH3CH2CH2CHCOOH

有机化学英文课件

有机化学英文课件

+ C H 3 C H 2 -O -H + C H 3 C H 2 -O -H
SN 2
+ C H 3 C H 2 -O -C H 2 C H 3 + O -H
H
H
H
A new oxonium ion
11-11
Preparation of Ethers
Step 3: proton transfer to solvent completes the reaction
+
CH 3 CH 2 -O -CH 2 C H 3 + O -H
H
H
proton tran sf er
+ CH 3 CH 2 -O -CH 2 C H 3 + H O -H
H
11-12ቤተ መጻሕፍቲ ባይዱ
Preparation of Ethers
Acid-catalyzed addition of alcohols to alkenes
Acid-catalyzed dehydration of alcohols
• diethyl ether and several other ethers are made on an industrial scale this way
• a specific example of an SN2 reaction in which a poor leaving group (OH-) is converted to a better one (H2O)
CH 3 CH3C=CH2 + H
+ O CH3
H
CH3 C H 3 C+C H 3 +

(完整版)Chapter14,15

(完整版)Chapter14,15

十四章土壤及其应用Soil and land are not the same. Land is the part of the world not covered by the oceans. Soil is a thin covering over the land consisting of a mixture of minerals, organic material, living organisms, air, and water that together support the growth of plant life.土壤和陆地是不同的。

陆地是地球上未被海洋覆盖的部分。

土壤是陆地上一层薄的覆盖层，由矿物质、有机质、活的生物体、空气和水组成的混合物，这些物质一起支持植物的生长。

A combination of physical, chemical, and biological events acting over time is responsible for the formation of soil.土壤的形成涉及一系列物理、化学和生物过程。

The organic material resulting from the decay of plant and animal remains is known as humus.植物和动物残骸分解产生的有机物质称为腐殖质。

Soil properties include soil texture, structure, atmosphere, moisture, biotic content and chemical composition. Soil texture is determined by the size of the mineral particles within the soil.土壤的性质包括土壤的质地、结构、含气量、水分、生物和化学组分等。

Chapter 14 Ethers, Epoxides, and Sulfides 有机化学英文版教学课件(美国达拉斯社区学院) 《Organic Ch

Chapter 14 Ethers, Epoxides, and Sulfides 有机化学英文版教学课件(美国达拉斯社区学院) 《Organic Ch

formed.
Chapter 14
=> 18
Phenyl Ether Cleavage
• Phenol cannot react further to become halide.
• Example:
OC H 2C H 3 H B r
O H +C H 3C H 2 B r
=>
Chapter 14
19
=>
Chapter 14
13
Phenyl Ethers
• Phenoxide ions are easily produced for use in the Williamson synthesis.
• Phenyl halides or tosylates cannot be used in this synthesis method.
• These are the same products that were formed in acid.
• Different products are formed in acid and base if epoxide is unsymmetrical. =>
Chapter 14
28
Orientation of Epoxide Opening
• Precautions:
➢Do not distill to dryness.
➢Store in full bottles with tight caps. =>
Chapter 14
20
Sulfides (Thioethers)
• R-S-R, analog of ether
• Name like ethers, replacing “sulfide” for “ether” in common name, or “alkylthio” for “alkoxy” in IUPAC system.

IG补课用Chapter 14 organic chemistry(完整版课件)

IG补课用Chapter 14 organic chemistry(完整版课件)

5.aliphatic（脂肪族的，无环的） alcohols and ketones (are named in a similar way to alkene)
CH3CH2CH2OH
propan-1-ol
H OH H H CCC H
H HH
propan-2-ol
CH3CH2COCH2CH3 pentan-3-one
Carboxylic acid 羧酸
ester 酯
benzene
-X,where X=F、Cl、 Br、I
chloromethane
-OH
methanol
ethanal
propanone
ethanoic
ethyl ethanoate
amine胺 nitrile腈
-NH2
methylamine
YCIC AS Organic Chemistry
2. π bond
① π bonds are formed by sideways overlap of p orbitals.原子轨道“肩 并肩”重叠。
② π bonds are not symmetrical about a line jointing the nuclei of the atoms forming the bond.
e.g ethane molecular formula: C2H6 Exercise： 1.propane 2.ethanoic acid
3.butanol
C3H8
C2H4O2
C4H10O
YCIC AS Organic Chemistry
3.Structural formula(结构式）
Denefition: the formula that tell us about the atoms bonded to each carbon atom in an

14第十四章 醇、酚、醚

14第十四章 醇、酚、醚

ONO2
CH2 ONO2
CH ONO2
CH2 ONO2
+ 3H2O
4、山梨醇和甘露醇
山梨醇和甘露醇都是六元醇， 二者是异构体。它们都是白 色结晶粉末，味甜，广泛存 在于植物中，如许多水果及 蔬菜中均含有。山梨醇和甘 露醇均易溶于水。它们的 20%或25%的溶液，在临床 上用作渗透性利尿药，能将 周围组织及脑组织的水分吸 入血中随尿排出，从而降低 颅内压，消除水肿，对治疗 脑水肿与循环衰竭有效。
⑵ 分子间脱水——单醚的合成
CH3CH2OH + HO CH2CH3
H2SO4 170℃
H2SO4 140℃
CH2
CH3CH2OCH2CH3 + H2O
比较：
CH3CH2OH
CH2 + H2O
反应条件决定反应产物； 醇的分之间脱水用于制备简单醚（简称单醚），但 不适合制备混合醚。 比较：Williamson混合醚合成法
R OH + H
O CH3OH + HO S O OH
ONO2
RONO2 + H2O
硝酸酯
－H2O CH3O O S O OH CH3OH CH3O O S O OCH3 + H2O
硫酸氢甲酯
CH2 OH
CH OH
CH2 OH
+ 3HONO2
CH2 ONO2
硫酸二甲酯：有机合成 中重要的甲基化试剂， 但有剧毒！ CH CH2 + 3H2O ONO2 ONO2
① 状态：大多数为无色固体，但易被空气中的氧气氧化而产 生有色杂质； ② 溶解性：可部分溶于水（为什么？），羟基越多，水溶性 越好，易溶于有机溶剂。
三、酚的化学性质chemical properties

有机化学 Chapter 14 organometal

有机化学 Chapter 14 organometal

§14.3 Preparation of organometallic compounds
A, Organolithium compounds
B, Organomagnesium compounds (Grignard reagent)
Aryl and vinyl chlorides don’t form Grignard reagents in diethyl ether. However, when THF is used as the solvent, they are okay.
2. Alkane synthesis
Primary alkyl halides, especially iodides, are the best substrates
Secondary and tertiary halides encounter elimination side reaction
§14.4 Organolithium & organomagnesium compounds as Brønsted bases
Organolithium and organomagnesium compounds are stable species They are strongly basic, and react instantly with proton donors even alcohol and water
Example:
环丙基锂
二乙基镁
When the metal bears a substituent other than carbon, the substituent is treated as if it were an anion and named separately:

有机化学(英文影印版)-chapter+4+Teaching+Contest

有机化学(英文影印版)-chapter+4+Teaching+Contest
Include in brackets beginning with the largest bridge and proceed to the shortest identifying the number of carbons in
each bridge and include in brackets.
• Nomenclature of straight chain alkanes
• Nomenclature of alkyl groups • Nomenclature of branched alkanes • Nomenclatures of simple cycloalkanes
3
Definition of Alkanes and Cycloalkanes • Alkanes:
• Characteristics of Alkanes
– Hybridization of Carbons = SP3 – Geometrical Molecular Shape = Tetrahedral – Bond Angles = 109º – Polarity = Non-Polar
2
• Definition of alkanes and cycloalkanes
CH3 CH2CH3 CH3 C CH3 CH CH2 CH2
(3-ethyl-4,4-dimethy)pentyl
9
Nomenclature of Branched Alkyl Groups
• -CH(CH3)2 • -CH(CH3)CH2CH3 1-methylethyl (isopropyl) 1-methylpropyl (sec-Butyl)
Chapter 4

有机化学(OrganicChemistry)-讲稿

有机化学(OrganicChemistry)-讲稿

CH3CH2C(CH3)2
HCl
2021/1/2
32
H 原子的相对活性：比较C-H键 能（离解能）的大小越小越易断
2021/1/2
33
再举例
2021/1/2
34
提醒：H原子的类型 --反应涉及到C-H键的断裂； H原子的活性（易断）--叔氢>仲氢>伯氢; 烃基(碳基R)的类型--反应涉及到 烃基R(自由
2021/1/2
19
C H SP3 1S
C C SP3 SP3
例子：甲烷分子CH4结构图
2021/1/2
20
4. 烷烃的同分异构体:
5. 同分异构体的类型:
6. (1.) 结构(构造)异构---因分子中原子不同排列顺
序而产生的; 例:烷烃的碳链异构
7.
丁烷分子式是C4H8 有正丁烷 CH3CH2CH2CH3
2021/1/2
14
(3.)SP杂化：
PY PZ
说明C原子是二价等同的
每个SP 是仍是胡芦形;二个SP组合在一起是水 线的, SP与SP杂化原子轨道间夹角是180度;留 下两个互相垂直的P哑铃轨道与SP杂化原子轨 道也垂直;
2021/1/2
15
*有机化学中碳原子轨道杂化总结
• 凡是C—C单键（饱和碳原子-烷烃）均为SP3杂 化，得四个SP3胡芦组合在一起是四面体结构 （109.5度）
18
饱和链烃（烷烃---Alkane)
一.结构
1.通式: CnH2n+2 n=1 CH4; n=2 CH3-CH3; n=3 CH3CH2CH3 etc. 2. 结构---透视式:
H
H
H
H
C H
H

有机化学 英文课件 chapter(3)

有机化学 英文课件 chapter(3)
6-11
Energy Diagram
A two-step reaction with one intermediate
6-12
Developing a Reaction Mechanism
How it is done
• design experiments to reveal details of a particular chemical reaction
6-14
Electrophilic Additions
• hydrohalogenation using HCl, HBr, HI • hydration using H2O in the presence of H2SO4 • halogenation using Cl2, Br2 • halohydrination using HOCl, HOBr • oxymercuration using Hg(OAc)2, H2O followed by
Addition is regioselective
• regioselective reaction: an addition or substitution reaction in which one of two or more possible products is formed in preference to all others that might be formed
• summary of the relationships between DG0, DH0, DS0, and the position of chemical equilibrium
M acin to sh P IC T im ag e fo rm at

有机化学基础英文版

有机化学基础英文版

3
CH3
1
Is 5-(1’-methylethyl)-2,2,4-trimethyloctane
CH3 CH3
Is 4,5-diethyl-2,2-dimethylheptane
It is NOT 3,4-diethyl-6,6-dimethylheptane!
4
H3C
H2 C
2
CH OH
CH3
4
H3C
R C O R
I
Bromide
R C O NH2
Iodide
R C O Cl
Carboxylic acid
R C O O C O
Ester
R R C N
Ketone
H R N R O O
Amide
Acid Chloride
Anhydride
Imine
Nitro groupFra bibliotekA cyclic ester is called a lactone, a cyclic amide a lactam
The ‘substitution level’ of a carbon atom in an organic compound is determined by the number of attached hydrogen atoms:
tertiary carbon (one H)
H3C H2 C H3C C H2 CH3 CH CH CH CH3 H2 C C CH3 CH3 CH3
CH3 CH C H2 CH3
is 3-methyloctane, not 5-methyloctane
2'
H3C
major chain

有机化学 英文课件 chapter

有机化学 英文课件 chapter
is n o t s u p p o r te d
9-14
Mechanism - SN1
9-15
Evidence of SN reactions
1. What is relationship between the rate of an SN reaction and:
• the structure of Nu? • the structure of RLv? • the structure of the leaving group? • the solvent?
M a c in to s h P IC T im a g e fo rm a t
is n o t s u p p o rte d
9-17
Kinetics
For an SN2 reaction,
• reaction occurs in one step • the reaction leading to the transition state involves the
haloalkane and the nucleophile • the result is a second-order reaction; first order in
haloalkane and first order in nucleophile
M a c in to s h P IC T im a g e fo rm a t
9-16
Kinetics
For an SN1 reaction
• reaction occurs in two steps • the reaction leading to formation transition state for

有机化学竞赛课件第14章 羧酸-2

有机化学竞赛课件第14章 羧酸-2

2Байду номын сангаас
CO2H + HgO + 2Br2
环丙基甲酸
2
Br + HgBr2 + 2CO2 + H2O
环丙基溴 41%~46%
二、还原
羧酸中的羰基在羟基的影响下，活性降低，一般情况 下不起醛酮中羰基所特有的加成反应。醛酮中的羰基容易 被还原，而羧酸只能用还原能力特别强的试剂还原。
O C17H35COH
硬脂酸
O
3RCOH + PCl3
3RCCl + P(OH)3
制备高碳芳酰氯； 亚磷酸, 200℃分解
易分离出OPCl3
O
O
3RCOH + PCl5
O
3RCCl + POCl3 + HCl
O 三氯氧磷, 沸点107℃
RCOH + SOCl2
RCCl + SO2 + HCl
注意: 反应需在无水条件下进行。
四、酸酐的生成
O R C OH
O+
-H+
R C OH
O R C OR'
R'
2、 酯化反应可逆，可采取使一种原料过量，或反 应过程中除去一种产物的方法来提高酯的产率。
3、酯化反应的速率决定于醇和羧酸的结构。
(1)对于同一羧酸，伯醇的酯化速率大于仲醇，仲醇 则远大于叔醇。
(2)同一类型的醇，分子量加大，酯化速率减慢。
§14.6 二元羧酸
低级的直链二元羧酸广泛存 在于自然界中。草酸的钾盐存在 于大黄等植物中，琥珀酸存在于 琥珀、真菌和地衣中，戊二酸和 己二酸存在于甜菜中。
二元羧酸中每一个羧基的反应都与一元羧酸相近。此 外，二元羧酸还有一些反应与两个羧基的相对位置有关。 一、 二元羧酸的酸性

Chapter 14 Ethers, Epoxides, and Sulfides 有机化学英文版

Chapter 14 Ethers, Epoxides, and Sulfides 有机化学英文版

H 2 S O 4
C H 3 C H 2O H +H O C H 2 C H 3
C H 3 C H 2O C H 2 C H 3
140°C
Chapter 14
=>
16
Cleavage of Ethers
• Ethers are unreactive toward base, but protonated ethers can undergo substitution reactions with strong acids.
200C3h,apPterre1n4tice Hall
1
Introduction
• Formula R-O-R where R is alkyl or aryl. • Symmetrical or unsymmetrical • Examples:
CH3 O CH3
O
O CH3 =>
Chapter 14
H
H
H
H
OCH3
• 1,2-Dihalide formed with HI or HBr. =>
Chapter 14
25
Biosynthesis of Steroids
Chapter 14
=>
26
Ring Opening in Base
Epoxide’s high ring strain makes it susceptible to nucleophilic attack.
• Alkoxide ion + 1 alkyl bromide (or tosylate)
• Example:
CH3 CH3 O H +

14 糖类

14 糖类

L-半乳糖
L-塔13罗糖
思考：如何确定－OH在手性碳的左边还是右边呢？
CHO H OH H OH
CH2OH 赤藓糖
HNO3
COOH H OH H OH
COOH
无旋光性 内消旋体
故： OH 在右边
CHO HO H
H OH
CH2OH 苏阿糖
HNO3
COOH HO H
H OH
COOH
有旋光性
故： OH 在左边
甘油醛（丙醛糖）
CH2—C—CH2 OH O OH
丙酮糖
CHO CHOH CHOH CHOH CHOH CH2OH
己醛糖
CH2OH C=O CHOH CHOH CHOH CH2OH
己酮糖
Chapter 14
4
2. 分类
糖
单糖—— 最简单的糖，不能再被水解的碳水化合物， 如葡萄糖等 特点：白色结晶，一般有甜味，可溶于水。
CHO
OH CH2OH
D-葡萄糖
Chapter 14
CH2OH C=O
自然界中存在的糖通常是D－型的。
OH CH2OH
D-果糖
16
单糖的绝对构型和标记(R/S)
对映体的构型可用R、S标记
如 D-(+)-葡萄糖
CHO 1
H-C-OH 2 R HO-C-H 3 S
H-C-OH 4 R H-C-OH 5 R
是糖类，但分子式中 H:O ≠ 2:1
甲醛 CH2O 乙酸 C2H4O2 乳酸 C3H6O3
化学结构上符合通式，但 化学性质上都不属于糖类
Chapter 14
3
定义：从结构上看，糖是指多羟基醛或多羟基酮及其 缩合物，或水解后能生成多羟基醛或多羟基酮的一类 有机化合物。

有机化学英文课件chapter12-31页文档资料

有机化学英文课件chapter12-31页文档资料
is n o t s u p p o rte d
12-24
IR of Molecules with C=O Groups
M acintosh P IC T im age form at
is not supported
12-25
Aldehydes and Ketones
u IR spectrum of menthone (Fig 12.12)
• the total energy is proportional to the frequency of vibration
• the frequency of a stretching vibration is given by an equation derived from Hooke’s law for a vibrating spring
12-8
Molecular Vibrations
u For a molecule to absorb IR radiation
• the bond undergoing vibration must be polar and • its vibration must cause a periodic change in the bond
12-26
Carbonyl groups
u The position of C=O stretching vibration is sensitive to its molecular environment
• as ring size decreases and angle strain increases, absorption shifts to a higher frequency

有机化学(OrganicChemistry)-讲稿

有机化学(OrganicChemistry)-讲稿

CH3COOCH2CH3 H2O
CH3COOCH2CH（3 主产物）
CH3COOC要反应方式) 例:AB是双原子(一个共价单键)分子,断裂时
主要以下列两种方式进行,
AB (A B)
A
B (均裂;是自由基或游离基反应)
A
B
A B (异裂;是离子化反应)
*离子化反应也称为Lewis酸碱反应
(1.) 键长: (2.) 键角: (3.) 键能: (4.) 键极性(分子极性和元素电负性): 五. 有机化合物的分类 六.研究有机化合物的一般程序
2019/11/18
17
第二章 饱和烃 （SaturatedHydrocarbon)
烃: 仅仅含有C和H两元素组成,
开链烃 (脂肪烃)
饱和烃(烷烃) 如CH3－CH3
1.分子结构的确定:
(1.) 分子中原子排列顺序的确定;
(2.) 分子中原子在空间的排列方式(即分 形状) 确定; 例:
C3H8 T: CH3CH2CH3 F: CH3CH3CH2
子的
C4H8 T: CH3CH CHCH3 ; F; CHCH3 CHCH3
H
CH3
H
H
T:
CC
CH3
H
CC
CH3
CH3
组成（Component)
物质
结构(Structure) 性质（ Properties)
应用(Application)
无机化学 分支 有机化学
分析化学
(2.)有机化学: 研究有机物的化学 (3.)有机物(Organic Compounds)
主元素：C，H；
一类碳氢化合物（只含主元素，又称为烃）
2杂01元9/1素1/1：8 X，O，S，N，P； 及其衍生物（含有杂元素，又称烃的衍生物） 2
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R R
C=O
HSH-CHH+2O2CH2SHcycRlRicCthiSSoacet-RaHlaSnCeyHN2Ci(HH22S) H
R R
CH2
The reduction of C=O groups of aldehydes and ketones into
CH2 group: Clemmensen reduction: Zn(Hg)/HCl, △ Wolff-Kishner reduction: NH2NH2/NaOH/(HOCH2CH2)2O, △ Reduction of aryl alkylketone: H2/Pd (neutral condition) Reduction of thioacetals: Raney Ni(H2)
9
d. Addition of ammonia and its derivatives (H2NX)
NH2NH2
H2NNH
O2N H2NNH
O2N
hydrazine phenylhydrazine 2,6-dinitrophenylhydrazine
肼
苯肼
2,6-二硝基苯肼
O
O
H2NCNH 2
H2NNHCNH 2
central C of an acyl group will benefit the nucleophilic addition. 2) Steric hindrance—The less steric hindrance of the central C will increase the reaction rate of nucleophilic addition.
+H2O R
+
C OR'
H
R'OH R'OH
R H
C
+
H OR'
OR'
H+
+
+H3O
R C
OR'
H OR'
ac etal缩醛
stable in basic solution
HO R'
R C=O +
R
CH CH
HO R'
H2SO4(conc.) H3O+
RO C
RO
R' R'
cyclic ketals 环缩酮
+
CCH3 CH3
-
H3O HOCH2CH2OH
O
O" CCH3Biblioteka CH3MgClOH
C-CH3 CH3
8
c. Addition of thiols (mercaptan RSH)
R C=O
R
H+ 2RSH -H2O
R SR Raney Ni(H2)
C R SR
- 2RSH
thioacetal
R R CH2
R' OH
R or R’ = H hemiacetal
半缩醛
HOCH2CH2CH2CH2C
O H
C O+
O H
H
C O
OH H
6
R C
OH
H OR'
hemiac etal
HCl(gas)
or H2SO 4(conc.)
H+
R H
C
+
H O.. H
O. . R'
R + .. H2O H C O..R'
hydrocyanic acid sodium bisulfite
OH
R C=O + H2O
H
R OH C
H OH
gem-diol hydrate
Cl3CCH OH
chloral hydrate
水合三氯乙醛
hypnotic
The study on the mechanism of this reaction:
carbamide(urea) semicarbazide
尿素
氨基尿素
O
H2NNHCNHNH 2
carbazide
卡巴肼
H2NOH
RR'C=NR"
C=C NRR'
R'
Nu
C=O
R
Nu
C R'
R
O+
R' RCO
Nu
H+
Nu
R'
R' C OH + R C OH
R
Nu
1
b. Weak nucleophiles with acidic catalysts (acidic conditions)
R'
H+
CO
R
-H+
R'
C R
+ HNu OH
Nu R'
R' C OH+ R
Chapter 14 Addition to the Carbonyl Group
14.2 General mechanism of nucleophilic addition to the carbonyl groups of aldehydes and ketones
a. Strong nucleophiles without catalysts (basic conditions)
Ph C=O
H5C2
H3C
Ph
H3C C O
A
H3C C O
NO2 B
H3C C O
CH3 C
H3C CH3 C
O D
4
14.4 14.5 14.9 14.10 The addition of H20, ROH, RSH, H2NX, HCN, NaHSO3
a. Addition of water
3
The general order of the reaction rate of the nucleophilic addition of carbonyls is as follows:
H C=O >
H3C C=O >
Ph
H3C C=O > C=O >
O>
H
H
H
H3C
H5C2 C=O >
Ph C=O >
+
NuH
R'
R' C OH + R
R
C OH
C OH NuH
+
R
Nu
HNu = H2O, HOR, NH3, HNR2
2
c. Reactivity of aldehydes and ketones towards nucleophilic addition
Two factors: 1) Electronic effect—The more electron-deficient
O16 C-C-C
H2O18
16O +
C-C-O18H2
C
16OH 18
C-C-OH C
-H2O16 H2O16
O18 C-C-C
5
b. Addition of alcohols
R
C=O + HOR" R'
H R C O+ R" R' O
R,R’ = alkyl
hemiketal
R OR"
半缩酮
C
7
To make the following synthesis:
from O
O COC2H5 to O
O
O COC2H5
+
H
HOCH2CH2OH
O O
OH C-CH3 CH3
O COC2H5
CH3MgCl
"O O
OMgCl " COC2H5
H5C2OMgCl "
CH3
O O
" O O
OMgCl "