Organic Chemistry: Principles And Mechanisms
Organic Chemistry: Principles And Mechanisms
2nd Edition
ISBN: 9780393663549
Author: KARTY, Joel
Publisher: W. W. Norton and Company
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Chapter E, Problem E.14P
Interpretation Introduction

(a)

Interpretation:

The IUPAC name for the given compound including stereochemical designations is to be assigned.

Concept introduction:

In naming organic compounds, the functional groups other than the highest priority functional groups are treated as substituents. Remove the “e” from the normal ‘ane’, ‘ene’, or ‘yne’ ending and add the suffix that corresponds to the highest-priority functional group. The root name is established by identifying the longest carbon chain or a ring containing a functional group. Number the carbon chain in a way the functional group and the substituents attached gets the lowest number. The position of functional group and substituents on parent chain or ring is indicated by the respective locant number. Prefixes are used to denote the number of identical substituents. The substituents are written in alphabetical order when writing the IUPAC name.

The stereochemical designation and the locators are enclosed in parentheses at the very beginning of the name. The stereochemistry at the chiral center is determined by assigning the priorities to the groups attached to the chiral center on the basis of an atomic number of directly bonded atom. If the sequence of priority order 123 is clockwise the absolute configuration is R and if it is counterclockwise the absolute configuration is S. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond where the same priority groups are on the opposite side of the double bond. Z represents the cis double bond where the same priority groups are on the same side of double bond.

Interpretation Introduction

(b)

Interpretation:

The IUPAC name for the given compound including stereochemical designations is to be assigned.

Concept introduction:

In naming organic compounds, the functional groups other than the highest priority functional groups are treated as substituents. Remove the “e” from the normal ‘ane’, ‘ene’, or ‘yne’ ending and add the suffix that corresponds to the highest-priority functional group. The root name is established by identifying the longest carbon chain or a ring containing a functional group. Number the carbon chain in a way the functional group and the substituents attached gets the lowest number. The position of functional group and substituents on parent chain or ring is indicated by the respective locant number. Prefixes are used to denote the number of identical substituents. The substituents are written in alphabetical order when writing the IUPAC name.

The stereochemical designation and the locators are enclosed in parentheses at the very beginning of the name. The stereochemistry at the chiral center is determined by assigning the priorities to the groups attached to the chiral center on the basis of the atomic number of directly bonded atom. If the sequence of priority order 123 is clockwise the absolute configuration is R and if it is counterclockwise the absolute configuration is S. The fourth priority group pointing towards the observer reverses the configuration.

Interpretation Introduction

(c)

Interpretation:

The IUPAC name for the given compound including stereochemical designations is to be assigned.

Concept introduction:

In naming organic compounds, the functional groups other than the highest priority functional groups are treated as substituents. Remove the “e” from the normal ‘ane’, ‘ene’, or ‘yne’ ending and add the suffix that corresponds to the highest-priority functional group. The root name is established by identifying the longest carbon chain or a ring containing a functional group. Number the carbon chain in a way the functional group and the substituents attached gets the lowest number. The position of functional group and substituents on parent chain or ring is indicated by the respective locant number. For the substituents attached to the amine nitrogen, the italic N is given as locator instead of a number. Prefixes are used to denote the number of identical substituents. The substituents are written in alphabetical order when writing the IUPAC name.

The stereochemical designation and the locators are enclosed in parentheses at the very beginning of the name. The stereochemistry at the chiral center is determined by assigning the priorities to the groups attached to the chiral center on the basis of an atomic number of directly bonded atom. If the sequence of priority order 123 is clockwise the absolute configuration is R and if it is counterclockwise the absolute configuration is S. The fourth priority group pointing towards the observer reverses the configuration.

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