BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD)
BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD)
8th Edition
ISBN: 9781337687539
Author: Brown/Iverson/Anslyn/ Foote
Publisher: CENGAGE C
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Chapter 5, Problem 5.33P

(a)

Interpretation Introduction

Interpretation:

Two different coiling patterns of the carbon skeleton of farnesol that can lead to form santonin have to be shown.

Concept Introduction:

Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.

Isoprene unit:

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 5, Problem 5.33P , additional homework tip  1

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 5, Problem 5.33P , additional homework tip  2

Branched end of isoprene – Head

Unbranched end of isoprene - Tail

(b)

Interpretation Introduction

Interpretation:

Chiral carbon atoms present in santonin has to be labelled and the number of possible stereoisomers for santonin has to be given.

Concept Introduction:

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

Number of possible stereoisomers for a compound can be determined as,

No of possible stereoisomers = 2nwhere,n = no. of chiral atoms in the compound

(c)

Interpretation Introduction

Interpretation:

Index of hydrogen deficiency has to be calculated for santonin.

Concept Introduction:

Index of hydrogen deficiency in a molecule is the total number of rings and π- bonds.

Index of hydrogen deficiency=(Hreference Hmolecule)2where,Hmolecule= Number of hydrogens in the given molecule.Hreference=Number of hydrogens in the acyclicalkane  having same number of carbon atoms(CnH2n+2).

The molecular formula of the reference hydrocarbon has to be adjusted if atoms other than carbon and hydrogen are present.

  • • If Group 7 elements like F, Cl, Br, I is present, then the halide atom is replaced by hydrogen. For example, the molecular formula of the acyclic monochloroalkane is CnH2n+1Cl, then the molecular formula should be taken as CnH2n+2.
  • • If Group 6 elements like O, S, Se are present, then there is no change in the molecular formula.
  • • If Group 5 elements like N, P, As are present, then one hydrogen should be added to the molecular formula.

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