Question

Difficulty: MediumFunctional Groups, Homologous Series, and IUPAC Nomenclature

Match each polyfunctional organic compound listed on the left with its principal IUPAC functional group suffix on the right, based on IUPAC nomenclature priority rules.

  • HOCH2CH2COOH\text{HOCH}_2\text{CH}_2\text{COOH}-oic acid
  • CH3COCH2CHO\text{CH}_3\text{COCH}_2\text{CHO}-al
  • CH3CH(OH)COCH3\text{CH}_3\text{CH(OH)COCH}_3-one
  • CH2=CHCH2OH\text{CH}_2=\text{CHCH}_2\text{OH}-ol

Answer

The correct pairings match HOCH2CH2COOH\text{HOCH}_2\text{CH}_2\text{COOH} with -oic acid, CH3COCH2CHO\text{CH}_3\text{COCH}_2\text{CHO} with -al, CH3CH(OH)COCH3\text{CH}_3\text{CH(OH)COCH}_3 with -one, and CH2=CHCH2OH\text{CH}_2=\text{CHCH}_2\text{OH} with -ol.
In IUPAC nomenclature for polyfunctional organic compounds, the principal functional group determines the ending suffix of the compound name. Carboxylic acid (COOH-\text{COOH}) outranks alcohol (OH-\text{OH}), giving -oic acid; aldehyde (CHO-\text{CHO}) outranks ketone (CO-\text{CO}-), giving -al; ketone (CO-\text{CO}-) outranks alcohol (OH-\text{OH}), giving -one; and alcohol (OH-\text{OH}) outranks alkene (C=C\text{C}=\text{C}), giving -ol.

Step-by-Step Solution

1
Identify all functional groups present in each compound.
Compound 1 contains hydroxyl and carboxyl; Compound 2 contains ketone and aldehyde; Compound 3 contains hydroxyl and ketone; Compound 4 contains alkene and alcohol.
Identifying all present functional groups is necessary before applying priority rules.
2
Apply standard IUPAC functional group seniority order.
Priority order: Carboxylic acid (COOH-\text{COOH}) > Aldehyde (CHO-\text{CHO}) > Ketone (CO-\text{CO}-) > Alcohol (OH-\text{OH}) > Alkene (C=C\text{C}=\text{C}).
The group with higher priority determines the principal suffix of the IUPAC name, while lower priority groups are named as prefixes.
3
Assign the principal suffix to each compound.
Compound 1 matches -oic acid, Compound 2 matches -al, Compound 3 matches -one, and Compound 4 matches -ol.
Matches each compound structure to its appropriate IUPAC ending based on priority.

Key Concept

IUPAC Functional Group Seniority Hierarchy
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