Question

OH Hom 유 용 The Tone The ♡ ♡ Tñ y OH H OH E OH F HO3 G Look at the given reaction and select the most appropriate answer from the dropdown menus to fill in the analysis. The substrate haloalkane is a secondary haloalkane. The nucleophile is a poor nucleophile. And the solvent is protic This means the reaction likely follows a(n) SN1 • mechanism(s), which will result in the stereochemistry at the reacting center being randomized - due to a planar carbocation intermedi e in the mechanism.

Dropdown Menus:

1. methyl, primary (unhindered), primary (hindered), secondary, tertiary

2. poor, weakly basic, strongly basic (hindered), strongly basic (unhindered)

3. protic, aprotic

4. SN2, SN1, E1, E2, SN2 AND E2, SN1 AND E1, No Reaction

5. randomized, inverted, predictable but not inverted, unchanged

6. a planar carbocation intermediate, backside attack transition state, anti-periplanar transition state, other

Answer 1

Explanation of Dropdown menus as the following.

1. Methyl group ( in wedge dark) is secondary,

due to it present on secondary carbon of haloalkane. hence your compound is secondary.

2. Water is poor nucleophile because , it does not donate lone pair of oxygen easily due to high electronegativity of oxygen. Hence it is poor nucleophile.

3. Water is protic solvent because it exist in ionized form of H+ and OH-. So H+ is easily giving. Those solvent which provide H+ easily are called protic solvent.

4. SN1 reaction due to in presence of protic solvent and also your carbocation is forming, which is proved by your product major and minor, Hence mechanism is SN1. Explanation is given as carbocation first form is secondary which is further rearranged to tertiary carbocation , Then your nucleophile is attacking either above or below the plane. The protic solvent work is here that it is doing hydration to carbocation , means water is also stabilizing your carbocation.

5. The product stereochemistry is racemic mixture that is randomized. Due to carbocation is planar so your nucleophile is attacking either above or below the plane. Giving two products.

6. Planar carbocation because SN1 reaction is giving carbocation, which have planar geometry due to this  H2O nucleophile attack either from above the plane or below the plane. And the product is racemic. This prove that carbocation is planar and also planar carbocation have sp² hybridization.