Questions: Give the IUPAC name for the following compound. (A) (E,R)-2-bromo-3-pentenoic acid (B) (Z,R)-2-bromo-3-pentenoic acid (C) (E,S)-2-bromo-3-pentenoic acid (D) (Z, S)-2-bromo-3-pentenoic acid

Give the IUPAC name for the following compound.
(A) (E,R)-2-bromo-3-pentenoic acid
(B) (Z,R)-2-bromo-3-pentenoic acid
(C) (E,S)-2-bromo-3-pentenoic acid
(D) (Z, S)-2-bromo-3-pentenoic acid

Transcript text: Give the IUPAC name for the following compound. (A) (E,R)-2-bromo-3-pentenoic acid (B) (Z,R)-2-bromo-3-pentenoic acid (C) (E,S)-2-bromo-3-pentenoic acid (D) $(Z, S)$-2-bromo-3-pentenoic acid

Solution

Solution Steps

Step 1: Identify the longest carbon chain

The longest carbon chain in the compound is a five-carbon chain with a double bond, making it a pentenoic acid.

Step 2: Number the carbon chain

Number the carbon chain starting from the carboxylic acid end to give the double bond the lowest possible number. The double bond is between carbon 2 and carbon 3, so it is a 2-pentenoic acid.

Step 3: Identify substituents and their positions

There is a bromo substituent on carbon 2, making it a 2-bromo-2-pentenoic acid.

Step 4: Determine the configuration of the double bond (E/Z)

The double bond configuration is determined by the priority of the groups attached to the double-bonded carbons. The higher priority groups on each carbon are on opposite sides, making it an (E) configuration.

Step 5: Determine the configuration of the chiral center (R/S)

The chiral center at carbon 2 has the following groups: Br, H, CH=CHCOOH, and CH3. Assign priorities based on atomic number and determine the configuration. The configuration is (R).