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Draw the structure of 2,2-dibromo-3-chlorohexanoic acid.

Chemistry

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  1. Identify the parent chain and 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\text{C}^{1}\text{OOH}-\text{C}^{2}-\text{C}^{3}-\text{C}^{4}-\text{C}^{5}-\text{C}^{6}

  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}): Already has 4 bonds (1 to C2, 1 double bond to O, 1 single bond to O, 1 single bond to H).
    • Carbon 2: Has 2 bonds (to C1 and C3). It needs 2 more bonds, which are taken by the two Br\text{Br} atoms. So, no hydrogens on C2.
    • Carbon 3: Has 2 bonds (to C2 and C4). It needs 2 more bonds. One is taken by the Cl\text{Cl} atom, so it needs 1 hydrogen.
    • Carbon 4: Has 2 bonds (to C3 and C5). It needs 2 hydrogens.
    • Carbon 5: Has 2 bonds (to C4 and C6). It needs 2 hydrogens.
    • Carbon 6: Has 1 bond (to C5). It needs 3 hydrogens.

  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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