Answered: 37. Which conditions favor an efficient… | bartleby

Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 21CTQ

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PROBLEM 27) Can you explain this problem and solve it correctly, please!

37. Which conditions favor an efficient (fast, high yield) SN2 reaction between an appropriate alkyl halide
and a nucleophile with a charge?
A. high concentration of a strong nucleophile, polar aprotic solvent
B. high concentration of a weak nucleophile, nonpolar solvent
C. low concentration of a strong nucleophile, polar aprotic solvent
D. low concentration of a weak nucleophile, nonpolar solvent
E. high concentration of a strong nucleophile, nonpolar solvent
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Rank the nucleophiles in each group in order of increasing nucleophilicity. a.−OH, −NH2, H2O b.−OH, Br−, F− (polar aprotic solvent) c.H2O, −OH, CH3CO2−
Identify the stronger nucleophile in each pair. a.NH3, −NH2 b.CH3NH2, CH3OH c.CH3CO2−, CH3CH2O−
Identify the stronger nucleophile in each pair. a. NH3,−NH2 b. CH3NH2, CH3OH c. CH3CO2−, CH3CH2O−
1. Attack the alkyl chloride with the stronger nucleophile. 2. Deprotonated to form the product
Identify the stronger nucleophile in each pair of anions. a.Br− or Cl− in a polar protic solvent b.HO− or Cl− in a polar aprotic solvent c.HS− or F− in a polar protic solvent
1. Nucleophilic addition involving H, CO 2. Nucleophile elimination ?
Identify the nucleophile and leaving group and draw the products of each substitution reaction.
Identify the nucleophile and leaving group and draw the products of each substitution reaction.
Which is a better nucleophile? a. Br or C in H20 b. Br or CI in DMSO c. CH3O or CH;OH in H20 d. CH30 or CH3OH in DMSO e. HO or NH2 in H20 f. HO or NH, in DMSO g. F or Br in H20 h. I or Br in DMSO
Draw the products of each reaction, and label the nucleophile and electrophile.
5. What halide is the strongest nucleophile in a polar aprotic solvent? Why? a. F-, Br-, Cl-, I- b. Br-, H20, TBUOK, CH3NH-
Which member of each pair is a better nucleophile in methanol? a. H2O or HO- b. NH3 or H2O c. H2O or H2S d. I- or Br- e. HO- or HS- f. Cl- or Br-

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