Question

Several reagents and several organic structures are shown below. Construct a multistep synthetic route for the synthe...

Several reagents and several organic structures ar

Several reagents and several organic structures are shown below. Construct a multistep synthetic route for the synthesis of acetylene from ethane by dragging the appropriate pieces into the bins. Note that each bin will hold only one item, and not every given reagent or structure will be used. (Stoichiometry is omitted.)

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Concept and reason

The concept used to solve this problem is using the given reagents, possible products will be formed in each step and then label it exactly in the given boxes in order to form the exact product.

Here, the starting reactant is ethane and the final product is acetylene.

Fundamentals

Sodium amide, is used as base, which abstract the proton.

NBS is used for the allylic bromination in the presence of peroxide.

Addition of HBr to alkene in the presence of peroxide forms an anti-Markovnikov’s product.

Bromine molecule is used for bromination of alkene. Trans addition takes place.

Bromination of alkane in the presence of sunlight gives radical substitution.

Potassium tertiary butoxide is a sterically hindered base.

The reaction is as follows:

Н2
Нас —с —Br
Br2
Нас —СНЗ
hv
ethane
bromoethane

The reaction is as follows:

(CH3)3CO K
Н2
Hас —с —вr
Hас—сH2
bromoethane
ethene

The reaction is as follows:

Br
Br
H2C
Нас— сН2
Н.с—сн,
1,2-dibromoethane
ethene

The reaction is as follows:

Br
2 NaNH2
НС— СH
Нас— сН2
acetylene
Br
1,2-dibromoethane

Ans:

The synthetic route for the synthesis of ethane to acetylene is labelled as follows:

H-C C-H
НаС—снз
(ethane)
(acetylene)
Step 1
Product
Reagent 3
Step 3
Product
Reagent 4
Reagent 1
Reagent 2
Step 2
Product
Br

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