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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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BuyFindarrow_forward

Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079
Textbook Problem

Each of the following ketones is named incorrectly. However, the names give correct structural formulas. What is the correct IUPAC name for each of these ketones?

  1. a. 4-Pentanone
  2. b. 2-Methyl-4-pentano
  3. c. 2-Ethyl-3-butanone
  4. d. 3,3-Diethyl-2-butanone

(a)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

  • • The longest parent carbon chain is identified that includes the carbonyl group.
  • • The parent chain name is changed by replacing the suffix “-e” with “-one”.
  • • Numbering is done in a way that the carbonyl group gets the least numbering.  The position of the carbonyl group is indicated in the name.
  • • The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.
  • • Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring.  The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.
Explanation

Given name of ketone is 4-pentanone.  From this name, it is understood that parent carbon chain is butane and the carbonyl carbon atom is the fourth carbon atom.  The structure of the ketone can be drawn as shown below,

The longest continuous carbon chain has to be found out with the carbonyl group in it.  In this it is a five carbon chain.  Hence, the parent alkane is pentane.  The ketone is named by replacing the suffix “-e” in the alkane name with “-one”...

(b)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

  • • The longest parent carbon chain is identified that includes the carbonyl group.
  • • The parent chain name is changed by replacing the suffix “-e” with “-one”.
  • • Numbering is done in a way that the carbonyl group gets the least numbering.  The position of the carbonyl group is indicated in the name.
  • • The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.
  • • Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring.  The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(c)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

  • • The longest parent carbon chain is identified that includes the carbonyl group.
  • • The parent chain name is changed by replacing the suffix “-e” with “-one”.
  • • Numbering is done in a way that the carbonyl group gets the least numbering.  The position of the carbonyl group is indicated in the name.
  • • The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.
  • • Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring.  The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(d)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

  • • The longest parent carbon chain is identified that includes the carbonyl group.
  • • The parent chain name is changed by replacing the suffix “-e” with “-one”.
  • • Numbering is done in a way that the carbonyl group gets the least numbering.  The position of the carbonyl group is indicated in the name.
  • • The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.
  • • Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring.  The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

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