Question

1,1-dibromo-4-methylhexane is treated first with excess sodium amide and quenched with water. catalytic hydrogenation affords what final product? (give correct iupac name.)

a) 4-methyl-2-hexene b) 4-methylhexane c) 3-methylhexane d) 4-methyl-1-hexene

Answer 1

The final product obtained is c).3-methylhexane.The product of catalytic hydrogenation of 1,1-dibromo-4-methylhexane is 3-methylhexane, due to the dehydrohalogenation followed by the reduction of the double bond without rearrangement.

Step-by-step explanation:

When 1,1-dibromo-4-methylhexane is treated with sodium amide, it undergoes a dehydrohalogenation reaction to remove the bromine atoms and form a double bond. Since there are two equivalents of bromine, the reaction will yield a diene. However, because the compound is then subjected to catalytic hydrogenation, the diene will be reduced to an alkane. As there is no opportunity for isomerization or rearrangement in a straightforward hydrogenation, the product will retain its original carbon skeleton. The correct IUPAC name for the hydrogenated product of 1,1-dibromo-4-methylhexane is 3-methylhexane. Therefore, the answer is (c) 3-methylhexane.