Question

Protecting groups are used in synthesis when a starting material contains multiple reactive sites. This neutralizes one of the reactive sites and makes it inert to the reaction conditions. The protecting group can then be selectively removed to re-form the reactive site. Analyze the molecule below and answer the three questions.

H3C CH3 Si CH3 CH3 CH3

Identify the protecting group.

Which reagent was used to install this protecting group?

Which reagent is used to remove the protecting group?

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Answer #1
Concepts and reason

If the starting material has more than one reactive site, protecting groups are used in organic syntheses to mask the undesired functional groups and make them inert to the reaction conditions. Finally, protecting groups are removed to regenerate the active sites back.

Fundamentals

The organic reactions are involved in the conversion of one functional group to another functional group in the starting material using a wide variety of reagents.

Protecting groups for alcohols:

H3C
CH3
-
CH₂
Ci
CH₃
H₃C
CH3
reagent
CH3
-
CH₂
Br
m
OH
r CH3
protection
starting material
CH3
starting material with protecti

(1)

Protection of alcohol functional group:

CH3
H3C
1
s
CHA
Br
CH3
CH3
starting material with protecting group

(2)

Reagent was used to install the given protecting group:

reagent
| Học
CH3
si
CH3
c1
X
CH3
CH3
Tert-butyldimethylsilyl chloride

(3)

Bu NF
reagent is used to remove the protecting group.

Tetra-n-butyl ammonium fluoride

Ans: Part 1

The protecting group is

•
TBDMS or
TBS ether
O
TIPS ether
O
TMS ether
O
THP ether

Part 2

The reagent used to install this protecting group is

O
triisopropylsilyl chloride
tert-butyldimethylsilyl chloride
dihydropyran
trimethylsilyl chloride

Part 3

The reagent used to remove the protecting group is

CH3MgBr
Bu N+F
H, Pd/C
KMnO4

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