FUNCTIONAL GROUP INTERCONVERSION

1. FUNCTIONAL GROUP INTERCONVERSION (FGI) in
nucleophilic aromatic substitution
PREPARED BY
RIMSHA BAKHTAWAR
MSC CHEMISTRY
10-5-2022

2. CONTENTS
• INTRO OF FGI IN SN REACTIONS
• SYNTHESIS OF ALCOHOL , ALKYL HALIDE , SULFONATES
• SYNHESIS OF ESTER , ETHER, AMINE
• SYNTHESIS OF AZIDE, NITRILE , ALKYNES
2
5/10/2021

3. The nucleophilic substitutions involve
the interconversion of functional groups bound to sp3
carbonis.
3
5/10/2021

4. There are three main sources to carry out FGI through
nucleophilic substitutions: sulfonates, alcohols, and alkyl
halides.
4
5/10/2021

5. A wide array of structures can be synthesized from sulfonates and alkyl halides through
nucleophilic substitution of X = OSO2R, I, Br, Cl in C–C bond forming reactions and FGI
5
5/10/2021

6. ALCOHOLS INTO ALKYL HALIDE
Tertiary alcohols react reasonably rapidly with concentrated hydrochloric acid, but
for primary or secondary alcohols the reaction rates are too slow reaction.
Other reagents for
alcohol conversions
PCl5
PBr3/ether
PI3
SOCl2/pyridine
PCl3
Ph3P, CCl4
For secondary and primary conversions
Other reagents for
R-X conversions
Aqueous KOH
H2O
NaOH , HIGH TEMP
6
5/10/2021

7. ALCOHOL SYNTHESIS
NITRATION
REDUCTION
DIAZOTIATION
HYDROLYSIS
7
5/10/2021

8. SULFONATE SYNTHESIS Using DMS and DES
is operationally
simple and scalable.
These two methods
are advantages bcz of
low cost, and
tolerated a wide
range.
sulfonate esters are
very good leaving
groups
(Finkelstein Reaction).
8
5/10/2021

9. OVERVIEW
• So if we know to synthesis and interconvert alcohol, alkyl halide and
sulfates we easily prepare our desired nucleophilic product in the
presence of specific nucleophilic reagents.
• From these three different reactions proceed.
9
5/10/2021

10. ALKYL HALIDE TO ESTER
10
5/10/2021

11. ALCOHOL TO ESTER
11
5/10/2021

12. ALKYL HALIDE TO ETHER
12
5/10/2021

13. ALCOHOL TO ETHER
13
5/10/2021

14. SYNTHESIS OF AMINE
14
5/10/2021

15. SYNTHESIS OF AZIDE
H2, Pd/C
B2H6
NaBH4
LiAlH4
Zn, HCl
(RO)3P
Ph3P
thiols
Reagents for N3 TO NH2
15
5/10/2021

16. SYNTHESIS OF ALKYNES
16
5/10/2021

17. NITRILE SYNTHESIS
DMSO
17
5/10/2021

18. REFERANCE
• https://www.chemistrysteps.com/preparation-of-carboxylic-acids/
• https://i.pinimg.com/originals/fe/bb/91/febb9111e0b538babfaee6a7
70fa882f.jpg
• https://www.masterorganicchemistry.com/2014/11/19/ether-
cleavage/
• https://chemisfast.blogspot.com/2020/03/benzyl-alcohol-to-benzoic-
acid-change.html
• https://www.vanderbilt.edu/AnS/Chemistry/Rizzo/chem223/FGI.pdf
18
5/10/2021

19. 19
5/10/2021