JEE Advance - Chemistry (2010 - Paper 1 Offline - No. 8)

The synthesis of 3-octyne is achieved by adding a bromoalkane into a mixture of sodium amide and and alkyne
BrCH2CH2CH2CH2CH3 and CH2CH2C $$\equiv$$ CH
BrCH2CH2CH3 and CH3CH2CH2C $$\equiv$$ CH
BrCH2CH2CH2CH2CH3 and CH3C $$\equiv$$ CH
BrCH2CH2CH2CH3 and CH3CH2C $$\equiv$$ CH

Explanation

To get appropriate bromoalkane an alkyne that were involved in the synthesis, we have to cleave the molecule and we know that sodium amide is involved, so the synthesis of 3-octyne using the alkyne and bromoalkane was $\mathrm{S}_{\mathrm{N}}2$ reaction. And as the sodium amide is involved, the alkyne involved must be terminal then only it could abstract the acidic hydrogen 3-octyne is a molecule that will have eight carbon atoms in their parent chain since the prefix-oct represents 8 and as in the name it is given that 3 octyne, ' 3 ' represents the position of triple bond. Thus suffix-one represents triple bond.

So, in the molecule triple bond will be at the third carbon. Structure of 3-octyne :

IIT-JEE 2010 Paper 1 Offline Chemistry - Hydrocarbons Question 27 English Explanation 1

Now, cleave the molecule between $\mathrm{C}_2-\mathrm{C}_3$ or $\mathrm{C}_4$ - $C_5$.

IIT-JEE 2010 Paper 1 Offline Chemistry - Hydrocarbons Question 27 English Explanation 2

Now, see the products formed if cleavage takes place between C2-C3, the reactants will be

IIT-JEE 2010 Paper 1 Offline Chemistry - Hydrocarbons Question 27 English Explanation 3

If cleavage takes place between C4-C5, the reactants will be :

IIT-JEE 2010 Paper 1 Offline Chemistry - Hydrocarbons Question 27 English Explanation 4

Then correct option is D.

IIT-JEE 2010 Paper 1 Offline Chemistry - Hydrocarbons Question 27 English Explanation 5

Comments (0)

Advertisement