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Draw the skeletal structure for 2,2-dibromo-3-chlorohexanoic acid.

Chemistry

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Step-by-step solution

5 steps
  1. Identify the parent chain and principal functional group.

    The name "2,2-dibromo-3-chlorohexanoic acid" indicates:

    • "hexan-" means a 6-carbon chain.
    • "-oic acid" means it is a carboxylic acid (COOH\text{COOH}), which is the principal functional group. The carbon of the carboxylic acid group is always designated as carbon 1.
  2. Draw the 6-carbon chain with the carboxylic acid group at carbon 1.

    C1OOH−C2−C3−C4−C5−C6\overset{1}{\text{C}}\text{OOH}-\overset{2}{\text{C}}-\overset{3}{\text{C}}-\overset{4}{\text{C}}-\overset{5}{\text{C}}-\overset{6}{\text{C}}
  3. Identify and place the substituents according to their locants.

    • "2,2-dibromo" means there are two bromine atoms (Br\text{Br}) attached to carbon 2.
    • "3-chloro" means there is one chlorine atom (Cl\text{Cl}) attached to carbon 3.
  4. Add hydrogen atoms to complete the valency of each carbon (4 bonds).

    • Carbon 1 (COOH\text{COOH}): This carbon is double-bonded to one oxygen, single-bonded to another oxygen (which is bonded to hydrogen), and single-bonded to carbon 2. It already has 4 bonds, so no hydrogens are attached directly to C1.
    • Carbon 2: This carbon is bonded to C1, C3, and two Br\text{Br} atoms. It has 4 bonds, so no hydrogens are attached to C2.
    • Carbon 3: This carbon is bonded to C2, C4, and one Cl\text{Cl} atom. It has 3 bonds, so it needs 1 hydrogen atom.
    • Carbon 4: This carbon is bonded to C3 and C5. It needs 2 hydrogen atoms.
    • Carbon 5: This carbon is bonded to C4 and C6. It needs 2 hydrogen atoms.
    • Carbon 6: This carbon is bonded to C5. It needs 3 hydrogen atoms.
  5. Assemble the full structure.

    Starting from the carboxylic acid end (C1):

    HOOC−C(Br)2−CH(Cl)−CH2−CH2−CH3\text{HOOC}-\text{C}(\text{Br})_{2}-\text{CH}(\text{Cl})-\text{CH}_{2}-\text{CH}_{2}-\text{CH}_{3}

    The structure of 2,2-dibromo-3-chlorohexanoic acid is:

    HOOC−C(Br)2−CH(Cl)−CH2−CH2−CH3\boxed{\text{HOOC}-\text{C}(\text{Br})_{2}-\text{CH}(\text{Cl})-\text{CH}_{2}-\text{CH}_{2}-\text{CH}_{3}}
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