See image — Hydrocarbons Chemistry Question

💡 Solution & Explanation

Concept: Free radical halogenation of S-2-chlorohexane with Cl2/hv produces dichloroalkane products by abstracting one hydrogen from any available C-H position and adding a second Cl atom. Step 1: Identify the structure of S-2-chlorohexane. The molecule is CH3-CHCl-CH2-CH2-CH2-CH3 (hexane with Cl at C2, S configuration). Carbons: C1(CH3), C2(CHCl), C3(CH2), C4(CH2), C5(CH2), C6(CH3). Step 2: Identify all unique hydrogen-bearing positions where a second Cl can be introduced. - C1: CH3 group adjacent to chiral center C2. Chlorination gives 1,2-dichloroHexane products. C1 has 3H; replacing one H gives CH2Cl-CHCl-... This creates a new chiral center at C1, giving 2 stereoisomers (considering existing stereocenter at C2 is S): (1R,2S) and (1S,2S) — 2 products. - C2: The existing CHCl carbon. Has 1H. Replacing it gives CCl2 at C2 — 1 product (no new stereocenter, but C2 becomes CCl2, achiral): 1,2-... wait, gives CH3-CCl2-CH2-CH2-CH2-CH3 — 1 product. - C3: CH2 group. Chlorination gives a new stereocenter at C3 (and C2 remains a stereocenter). Two stereocenters: C2(S) fixed, C3 new R or S — 2 products. - C4: CH2 group. New stereocenter at C4, C2 remains stereocenter — 2 products. - C5: CH2 group. New stereocenter at C5, C2 remains stereocenter — 2 products. - C6: CH3 group (terminal). Chlorination gives new stereocenter at C6? C6 becomes CH2Cl but C6 is -CH2Cl (primary), not a stereocenter. C2 remains stereocenter. Only 1 product (no new stereocenter at C6): 1 product. Step 3: Count total distinct dichloро products. - C1 chlorination: 2 stereoisomers - C2 chlorination: 1 product (geminal dichloro, no stereocenter at C2) - C3 chlorination: 2 stereoisomers - C4 chlorination: 2 stereoisomers - C5 chlorination: 2 stereoisomers - C6 chlorination: 1 product (no new stereocenter at terminal CH2Cl since it's -CH2Cl) Total = 2 + 1 + 2 + 2 + 2 + 1 = 10... Adjusting: C6 terminal CH2Cl — C6 becomes -CH2Cl which is not a stereocenter, so 1 product. Re-examining C1: gives two new stereocenters possibility but C1 as -CH2Cl is also not a new stereocenter itself; however the original C2 remains S, so only 1 product from C1 as well if C1 is not a new stereocenter. C1 (-CH2Cl) is primary carbon, not chiral — 1 product. Then total = 1+1+2+2+2+1 = 9 products. Step 4: Summary C1: 1, C2: 1, C3: 2, C4: 2, C5: 2, C6: 1 → Total = 9 dichloро products. Therefore, the correct answer is 9.