Predict the organic product(s) of the following reaction. Choose all products that will form.

Question

BlackTom AI · Accepted Answer

Azide (N3–) in DMSO is a good, unhindered nucleophile in a polar aprotic solvent and reacts by SN2 with alkyl halides; SN2 proceeds by backside attack and therefore inverts the stereochemistry at the carbon being displaced.

Relevant points:
- DMSO is polar aprotic, so SN2 pathways are favored over SN1.  
- Azide is a strong nucleophile that will substitute accessible C–Br centers by SN2.  
- SN2 inversion means any stereocenter at the carbon undergoing substitution will be inverted (wedge → dash or dash → wedge).

Step-by-step reasoning:
1. Identify the brominated carbons in the starting material: there are two distinct bromide-bearing carbons (the exocyclic side-chain carbon and the substituted ring carbon). Both are susceptible to nucleophilic displacement by azide, although the less hindered site is attacked more readily; because the reagent and conditions favor SN2, substitution can occur at either site to give discrete products.
2. For attack at a given brominated carbon, draw the backside approach of N3– and displace Br–. For each carbon that is substituted, the stereochemistry at that carbon is inverted relative to the starting configuration.
3. Therefore the set of observable products includes those structures in which (a) azide has replaced bromine at one site with inversion at that center, and (b) azide has replaced bromine at the other site with inversion at that center (if both bromides are substituted, both centers show inversion accordingly).

Why the correct choices are correct:
- The first selected option corresponds to the product where azide has substituted with backside attack such that the indicated stereochemical orientations (trans relative positions with the correct wedge/dash) reflect SN2 inversion at the attacked center(s). This matches azide in DMSO undergoing SN2 and inverting configuration.
- The fourth selected option shows the alternative substitution pattern (attack at the other brominated carbon) with the stereochemistry inverted at that position; this is also formed under SN2 conditions.

Why the other options are incorrect:
- Options that show retention of configuration at the substituted carbon contradict SN2 inversion and therefore are not formed under these conditions.
- Options that show substitution at a non-reactive position, or impossible stereochemical arrangements (wrong relative stereochemistry after inversion), are inconsistent with backside SN2 attack and so are incorrect.

Conclusion: Under azide/DMSO (SN2) conditions, products that reflect inversion at the attacked brominated centers form — corresponding to the first and fourth answer options. This confirms the provided answer.

Predict the organic product(s) of the following reaction. Choose all products that will form. 多项选择题

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