Question

Benzene can be converted to 1,3,5-tribromobenzene in five reaction steps and four intermediate compounds. Select the appropriate reagent from the drop-down list for each step in this overall synthesis.

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Step 1=?

Step 2=?

Step 3=?

Step 4=?

Step 5=?

Options for each step:

Br2, R2O2

CH3Cl, AlCl3

CH3COCl, AlCl3

NaNO2, HCl

HNO3, H2SO4

H3PO2

H3PO4

KMnO4

1) Sn, HCl; 2)OH-

Br2

1 1
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Answer #1
Concepts and reason

The concept is to synthesize 1,3,5-tribromobenzene from benzene by using the list of reagents provided.

Fundamentals

Given benzene can be converted to 1,3,5-tribromobenzene by using the following steps.

1.Nitration of benzene

2.Reduction

3.Bromination

4.Diazotization

5.Reaction of diazonium salt

The reaction is,

NO.
HNO3, H2SO4
benzene
nitrobenzene

The reaction is,

NO2
NH2
1) Sn, HCl; 2) OH
nitrobenzene
aniline

The reaction is,

NH2
NH2
Br
Br2
aniline
2,4,6-tribromoaniline

The reaction is,

NH2
V-
- Br
NaNO2, HCl
2,4,6-tribromoaniline

The reaction is,

N, C
Br
Br
H2PO2
Br
Br
1,3,5-tribromobenzene
2,4,6-tribromobenzenediazonium chloride

Ans:

Thus, the correct choice of reagents is,

Step-1: HNO3, H2SO4
Step-2: 1)Sn, HCl; 2)OH
Step-3: Br2
Step-4: NaNO2, HCI
Step-5: H2PO2

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