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Three reactions between a Grignard reagent and a carbonyl compound are given below. Draw the main organic product for each reaction and indicate if H+ or H- is needed to complete each reaction. (The starting material structures are provided in the answer fields as a starting point for your drawings.)

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Concepts and reason

The reagent which donates electrons and undergoes the formation of a new carbon – carbon bond is known as a Grignard reagent. Grignard reagent is an organometallic reagent with a formulaRMgX
. Here, represents alkyl group or aryl group, represents magnesium, and represents halogen. In this reagent, (alkyl group or aryl group) acts as nucleophile.

Fundamentals

In ketones, Grignard reaction undergoes two steps:

1)Nucleophilic attack

2)Protonation

Example:

0 MgBr
H+
R
R
-
K
R
R 4R
protonation
Hac— MgBr
nucleophilic attack on carbonyl carbon

In acid chlorides and ester, 2 equivalents of Grignard reagent react and form a new carbon – carbon bond. Then, this reaction undergoes nucleophilic attack twice cleavage of the leaving group occurs. This reaction proceeds in four steps:

1)Nucleophilic attack.

2)Removal of a leaving group.

3)Nucleophilic attack.

4)Protonation.

Example:

8 MgBr
R
R
CH
- TR
o
leaving group removal
H3C—MgBr
nucleophilic attack on carbonyl carbon
Brig —CH3
nucleophilic attack on

Part 1

MgBr
event
HC-MgBr

Part 2

°༽MgBr
CH3CH,-MgBr
CH3CH2-MgBr
OH
H+
MgBr

[Part 2]

Part 2

Part 3

MgBr
CH3CH2-MgBr
CH3CH2-MgBr

MgBr
OH
H

Ans: Part 1

MgBr
- int
H3C-MgBr

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