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Chapter 31: Question 31.12 (page 1250)

Write a stepwise mechanism for the following reaction.

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01

Diphosphate

Diphosphate is the oxyanion of phosphorus, and this compound contains two phosphate groups. It acts as a good leaving group (-OPP), and when two diphosphates are added, it forms geranyl diphosphate (10-C compound).

02

Stepwise mechanism

In the first step, the formation of a new C-C sigma bond occurs by the loss of diphosphate and then attack by isopentenyl diphosphate (nucleophile) on allylic carbocation.

In the second step, a new bond is formed by losing a proton.

Stepwise mechanism

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Most popular questions from this chapter

a. Draw a three-dimensional structure for the following steroid.

b. What is the structure of the single stereoisomer formed by reduction of this ketone with H2 , Pd-C? Explain why only one stereoisomer is formed.

(a) Draw a skeletal structure of the anabolic steroid methenolone from the following description. Methenolone contains the tetracyclic steroid skeleton with a carbonyl group at C3, a hydroxyl group at C17, a double bond between C1 and C2, and methyl groups bonded to C1, C10 and C13. (b) Add wedges and dashed wedges for all stereogenic centers with the following information: The configuration at C10 is R, The configuration at C13 is S, the configuration at C17 is S, and all substitutents at ring fusions are trans to each other. (c) Draw the structures of Primobolan, the product formed when methenolone is treated with CH3(CH2)5COCl and pyridine. Primobolan is an anabolic steroid that can be taken orally or by injection and has been used illegally by well-known Major League Baseball players.

Draw the enantiomer and any two diastereomers of cholesterol. Does the OH group of cholesterol occupy an axial or equatorial position?

A difficult problem in the synthesis of PGF2αis the introduction of the OH group at C15 in the desired configuration.

  1. Label this stereogenic center as R or S.

  2. A well known synthesis of PGF2αinvolves reaction of A with Zn((BH4)2a metal hydride reagent similar in reactivity toNaH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.

  3. Suggest a reagent to convert A to the single stereoisomer X.
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