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Question

What is the IUPAC name of the following compound?


A

1,1-dimethyl-1-bromo propene

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B

2-bromo-1-pentyne

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C

2-methyl-2-bromo-3-butene

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D

3-bromo-3-methyl-1-butene

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Solution

The correct option is D

3-bromo-3-methyl-1-butene


The explanation for the correct option:

(D) 3-bromo-3-methyl-1-butene

1. Determine the parent chain:

The given structure:

Identify the longest carbon chain:

First, the longest carbon chain is identified.

In this case, the longest carbon chain includes four carbon atoms.

Thus, the root word for the IUPAC name is “But”.

Identify the position of unsaturation (double bond):

The numbering should be done in a way that the double bond gets the lowest number.

Thus, the numbering should start from double bond in this compound.

The double bond is present between C-1 and C-2 position.

Identify the position of the substituents:

There is one methyl group and one bromo group present at C-3 position.

IUPAC Naming of the compound:

The IUPAC naming will be written in the order: Prefix+root word+suffix.

Prefixes are bromo and methyl. These substituents are written in the IUPAC name as per the alphabetical order along with their respective positions.

Root word is “but”.

Suffix is “-ene”.

Therefore, the IUPAC name of the compound is 3-Bromo-3-methyl-1-butene.

The explanation for the incorrect options:

(A) 1,1-dimethyl-1-Bromo propene

As per this name, the following structure can be drawn:

This structure does not match the given structure.

(B) 2-bromo-1-pentyne

As per this name, the following structure can be drawn:

This structure does not match the given structure.

(C) 2-methyl-2-bromo-3-butene

As per this name, the following structure can be drawn:

This structure does not match the given structure.

Therefore, the correct option is (D). The IUPAC name is 3-Bromo-3-methyl-1-butene.


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