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Bubblyparabola Bubblyparabola
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Question 1.

What is the predicted product when estradiol is treated with excess NaH followed by excess bromopropane?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1CC[C@@H]2O)O reacts with excess N a H in the first step and bromopropane in the second step.

An illustration shows the structures of four compounds. Compound 1 has four fused ring systems, in which the first is a benzene ring, the second and the third are cyclohexane rings, and the fourth ring is a cyclopentane ring. C 3 is single bonded to a hydroxyl group, C 8 is wedge bonded to a hydrogen atom, C 9 and C 14 are each dash bonded to a hydrogen atom, C 13 is wedge bonded to a methyl group, and C 17 is wedge bonded to an oxygen atom that is further bonded to C 1 of a three-carbon chain. Compound 2 has four fused ring systems, in which the first is a benzene ring, the second and the third are cyclohexane rings, and the fourth ring is a cyclopentane ring. C 3 is single bonded to an oxygen atom that is further bonded to C 1 of a three-carbon chain, C 8 is wedge bonded to a hydrogen atom, C 9 and C 14 are each dash bonded to a hydrogen atom, C 13 is wedge bonded to a methyl group, and C 17 is wedge bonded to an oxygen atom that is further bonded to C 1 of a three-carbon chain. Compound 3 has four fused ring systems, in which the first three are cyclohexane rings and the fourth ring is a cyclopentane ring. C 3 is single bonded to a hydroxyl group, C 8 is wedge bonded to a hydrogen atom, C 9 and C 14 are each dash bonded to a hydrogen atom, C 13 is wedge bonded to a methyl group, and C 17 is wedge bonded to a hydroxyl group. Compound 4 has four fused ring systems, in which the first is a benzene ring, the second and the third are cyclohexane rings, and the fourth ring is a cyclopentane ring. C 3 is single bonded to a hydroxyl group, C 4 is single bonded to a methyl group, C 8 is wedge bonded to a hydrogen atom, C 9 and C 14 are each dash bonded to a hydrogen atom, C 13 is wedge bonded to a methyl group, and C 17 is wedge bonded to a hydroxyl group.


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Question 2.

Which of the choices is a chair conformation for the compound shown?

The structure of the compound has four fused ring systems, in which the first three are cyclohexane rings and the fourth ring is a cyclopentane. C 3 is wedge bonded to a hydroxyl group, C 5, C 9, and C 14 are each dash bonded to a hydrogen atom, C 8 is wedge bonded to a hydrogen atom, C 10 and C 13 are each wedge bonded to a methyl group, and C 17 is double bonded to an oxygen atom.

An illustration shows the structures of five compounds. Compound 1 has four fused ring systems, in which the first three are cyclohexane rings and the fourth ring is a cyclopentane ring. C 3 is equatorially bonded to a hydroxyl group, C 5, C 8, C 9, and C 14 are axially bonded to a hydrogen atom, C 10 and C 13 are axially bonded to a methyl group, and C 17 is equatorially double bonded to an oxygen atom. The cyclohexane rings are depicted as chair conformations and the cyclopentane ring is depicted as a boat conformation. Compound 2 has four fused ring systems, in which the first three are cyclohexane rings and the fourth ring is a cyclopentane ring. C 3 is equatorially bonded to a hydroxyl group, C 5, C 8, C 9, and C 14 are axially bonded to a hydrogen atom, and C 17 is axially double bonded to an oxygen atom. The cyclohexane rings are depicted as chair conformations and the cyclopentane ring is depicted as a boat conformation.Compound 3 has four fused ring systems, in which the first three are cyclohexane rings and the fourth ring is a cyclopentane ring. C 3 is equatorially bonded to a hydroxyl group, C 10 and C 13 are axially bonded to a hydrogen atom, C 5 and C 14 are axially bonded to a methyl group, and C 17 is axially double bonded to an oxygen atom. The cyclohexane rings are depicted as chair conformations and the cyclopentane ring is depicted as a boat conformation. Compound 4 has four fused ring systems, in which the first three are cyclohexane rings and the fourth ring is a cyclopentane ring. C 3 is axially bonded to a hydroxyl group, C 5, C 8, C 9, and C 14 are axially bonded to a hydrogen atom, C 10 and C 13 are axially bonded to a methyl group, and C 17 is equatorially double bonded to an oxygen atom. The cyclohexane rings are depicted as chair conformations and the cyclopentane ring is depicted as a boat conformation. Compound 5 has four fused ring systems, in which the first three are cyclohexane rings and the fourth ring is a cyclopentane ring. C 3 is axially bonded to a hydroxyl group, C 8, C 9, C 10, and C 13 are axially bonded to a hydrogen atom, C 5 and C 14 are axially bonded to a methyl group, and C 17 is equatorially double bonded to an oxygen atom. The cyclohexane rings are depicted as chair conformations and the cyclopentane ring is depicted as a boat conformation.


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Textbook 
Organic Chemistry

Organic Chemistry


Edition: 4th
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Bubblyparabola Author
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3 years ago
Smart ... Thanks!
Lawson1981
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Just got PERFECT on my quiz
djeghri
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this is exactly what I needed
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