Welcome to Scribd, the world's digital library. Read, publish, and share books and documents. See more
Download
Standard view
Full view
of .
Look up keyword
Like this
2Activity
0 of .
Results for:
No results containing your search query
P. 1
31 ORGANIC CHEMISTRY 2 - Halogeno-Compounds and Grignard Reagents

31 ORGANIC CHEMISTRY 2 - Halogeno-Compounds and Grignard Reagents

Ratings: (0)|Views: 117 |Likes:
Published by Zara
Uploaded from Google Docs
Uploaded from Google Docs

More info:

Categories:Types, School Work
Published by: Zara on May 13, 2012
Copyright:Attribution Non-commercial

Availability:

Read on Scribd mobile: iPhone, iPad and Android.
download as PDF, TXT or read online from Scribd
See more
See less

11/15/2012

pdf

text

original

 
Organic Chemistry 2: Halogeno-compounds and Grignard ReagentsApril 2002Number 31
1
C
 hem
 F
 actsheet
To succeed in this topic you need to:-Have a good understanding of AS-level Organic Chemistry(Factsheets 15, 16, 17 and 27);Be confident in using organic nomenclature and structuralformulae.After working through this Factsheet you will:-Have reviewed the chemistry of the halogeno-compounds coveredso far;Know how Grignard reagents are formed;Know how Grignard reagents are used in a variety of organicpreparations.
Halogeno-alkanes
Fig 1 below summarises the reactions of the halogeno-alkanes.
Fig. 1
Halogenoalkane reactions
They contain a
δ
- carbon, which gives rise to the extremely reactive R
species i.e. in the above example,HCH
3
C
 
HThe R
species is a strong
nucleophile
, which is capable of attacking
δ
+carbons in other molecules - hence
carbon chain lengths can be increased.1. Reaction with water to form alkanes
R
MgI + H
2
O
R
H + Mg(OH)IReaction type:Substitution.Mechanism:Nucleophilic.This reaction shows why Grignard reagents must be prepared in dryconditions.
2. Reaction with methanal to form primary alcohol.
Methanal gas is passed into the solution of the Grignard, and the mixtureis then hydrolysed with dilute hydrochloric acid.R
MgI + CH
2
=O
R
CH
2
O
MgI (Nucleophilic addition)Then:R
CH
2
O
MgI + H
2
O
R
CH
2
OH + Mg(OH)I(Hydrolysis)Reaction conditions: In dry ether, followed by addition of dilute acid forhydrolysis.
3. Reaction with other aldehydes to form secondary alcohols.
R
MgI + R'CHO
CH
O
MgI CH
OH + Mg(OH)IReaction conditions: In dry ether, followed by addition of dilute acid forhydrolysis.For example:C
2
H
5
MgI + CH
3
CHO
CH
O
MgIC
OH + Mg(OH)IButan-2-ol
Grignard Reagents
The main focus of this Factsheet is on the formation and use of a commonlyexamined set of reagents derived from the halogenoalkanes - Grignardreagents.
Preparation of Grignard Reagents
Grignard reagents are prepared by refluxing alkyl or aryl bromide or iodidecompounds, dissolved in dry ether, with small magnesium turnings.R
Br + Mg
R
MgBr
 
'Grignard reagent'The Grignard reagent cannot be isolated - it must remain in etheral solutionfor further reaction.Example of Grignard reagent
preparation
:C
2
H
5
I + Mg
C
2
H
5
MgIReaction type:AdditionConditions:Dry ether solventRefluxTrace of iodine as catalystHalogenoalkane
nucleophilicsubstitution
nitrilealcohol
nucleophilicsubstitution
aminealkene
nucleophiliceliminationnucleophilicsubstitution
KCN inwater/ethanolheat underrefluxheatNH
3
inethanolNaOH(aq)heat underrefluxKOH inethanolheat underreflux
H
2
O
RR'RR'C
2
H
5
CH
3
C
2
H
5
CH
3
H
2
O
Reactions of Grignard reagents
The Grignard reagent is very reactive.H 
δ−
 
δ
+
CH
3
C Mg IH
www.curriculumpress.co.uk

You're Reading a Free Preview

Download
scribd
/*********** DO NOT ALTER ANYTHING BELOW THIS LINE ! ************/ var s_code=s.t();if(s_code)document.write(s_code)//-->