1. What is the electron donating group in the reaction shown? 2.What is the elec

Question

1. What is the electron donating group in the reaction shown?

2.What is the electrophilic substrate in the reaction shown?

3. Classify the electrophilic substrate (CH3,10,20,30, allylic, benzylic)

4. Classify the substrate (Hindered, Unhindered)

5. Classify the electron donating group (Weak Nucleophile/Weak Base/Hindered; Weak Nuc/Weak Base/Unhindered; Strong Nuc/Weak Base/Hindered; Strong Nuc/Strong base/Hind; Strong Nuc/Stron Base/Unhind; Strong Nuc/Weak Base/Unhind; Weak Nuc/Strong Base/Hind; Weak Nuc/Strong Base/Unhind)

6. Classify the solvent in this reaction (nonpolar, polar protic, polar aproitic)

7. What mechanism will dominate in this reaction? (SN2, E2, SN1/E1, none of these)

8. What are the regiochemical considerations for this mechanism with this reagent? (SELECT ALL THAT APPLY: Favors the more substitiuted product; favors less substituted product; favors rearrangement to more substituted product; Pi bond forms only between alph & beta carbons; reagent must form bornd to same carbon as leaving group)

9. What are the sterochemical consideration for this mechanism with this reagent? (SELECT ALL THAT APPLY: will always give inversion of stereocenter; will always give racemization of stereocenter; will favor the TRANS product; will favor the CIS product; leaving groups should be anti-coplanar unless eclipsed forced)

10. What is the major product of the reaction shown.

Explanation / Answer

1) Electron donating group is methoxide group ( -OCH3 from NaOCH3)

2) Electrophilic substrate is propylbromide ( CH3CH2CH2Br)

3) Electrophilic substrate is alkyl carbocation (C3H7+)

4) Substrate is unhidered as it is straight chain alkyl group, there is no substituent on any carbon.

5) Electron donating group is strong base/unhind

6) Solvent is polar protic solvent (CH3OH)

7) Methoxide ion is strong base so this reaction follows E2 elimination.Because substrate is primary alkyl halide.

8) Pi bond forms only between alph & beta carbons, because there is no chance to more substituted product.

9) leaving groups should be anti-coplanar unless eclipsed forced

10) Major product is propene. But it is not given in options, so other product is methanol (CH3OH) it is formed when methoxide take the proton from carbon. Answer is CH3OH.

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