1) Following are two diastereomers of 3-bromo-3,4-dimethylhexane . On treatment
ID: 974244 • Letter: 1
Question
1) Following are two diastereomers of 3-bromo-3,4-dimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexeneas the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives the E alkene?
2) Following are two diastereomers of 3-bromo-2,3,4-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 2,3,4-trimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives the E alkene?
3) Following are two diastereomers of 3-bromo-4-ethyl-2,3,5-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3-ethyl-2,4,5-trimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives the Zalkene?
Explanation / Answer
1) a:
In a, two methyl groups are on same side.
In the final product also, two methyl groups will be on same side.
Therefore,
a gives Z- alkene
b:
In b, two methyl groups are on opposite side.
In the final product also, two methyl groups will be on opposite side.
Therefore,
b gives E- alkene
2) a:
In a, two methyl groups are on same side.
In the final product also, two methyl groups will be on same side.
Therefore,
a gives Z- alkene
b:
In b, two methyl groups are on opposite side.
In the final product also, two methyl groups will be on opposite side.
Therefore,
b gives E- alkene
3) a:
In a, two isopropyl groups are on same side.
In the final product also, two isopropyl groups will be on same side.
Therefore,
a gives Z- alkene
b:
In b, two isopropyl groups are on opposite side.
In the final product also, two isopropyl groups will be on opposite side.
Therefore,
b gives E- alkene
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