CHM 2120 Lecture Notes - Lecture 14: Elimination Reaction, Cyclohexane Conformation, Nucleophile

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3 Nov 2016

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2 steps: leaving group leaves (rds), and carbocation forms (tertiary is most stable carbocation, base attacks neighboring hydrogen and this leaves a double bond to form between the alpha and beta carbons. Alkyl chain: tertiary preferred, with beta carbon being the more substituted one. Base: solvent may act as base, weak base so it waits for leaving group to leave on its own. So, if a base is weaker than the leaving group then the leaving group then type 1 happens because it is not strong enough to forcefully kick out the leaving group. There will always be competition between sn1 and e1. The beta carbon is the carbon closest to the alpha, we need to get most substituted alkene. Zaitse(cid:448)"s rule: the most substituted the alkene the more stable that alkene will be. There can be a cis, trans disubstituted alkenes. Tetrasubstituted is the most stable alkene that can form.

Related Questions

Determine certain aspects of the following reaction

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? (S_N2, E2, S_N1/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.

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)

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

7. What mechanism will dominate in this reaction? (S_N2, E2, S_N1/E1, none of these)

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

Questions 1 & 2 I need help with if possible?

CHM 2120 Lecture Notes - Lecture 14: Elimination Reaction, Cyclohexane Conformation, Nucleophile

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