For problem 8.17, all of the reactions will be SN2. For each reaction, identify and evaluate each nucleophile (strong? weak? Strong or weak as a base?) Also, evaluate each solvent as polar protic or polar aprotic. I recommend drawing the structure of each solvent. (g) Sodium methanethiolate (NaSCH3) in ethanol

For problem 8.17, all of the reactions will be SN2. For each reaction, identify and evaluate each nucleophile (strong? weak? Strong or weak as a base?) Also, evaluate each solvent as polar protic or polar aprotic. I recommend drawing the structure of each solvent. (g) Sodium methanethiolate (NaSCH3) in ethanol

EBK A SMALL SCALE APPROACH TO ORGANIC L

4th Edition

ISBN:9781305446021

Author:Lampman

Publisher:Lampman

Chapter20: Nucleophilic Substitution Reactions: Competing Nucleophiles

Section: Chapter Questions

Problem 2Q

See similar textbooks

Similar questions

For problem 8.17, all of the reactions will be SN2. For each reaction, identify and evaluate each nucleophile (strong? weak? Strong or weak as a base?) Also, evaluate each solvent as polar protic or polar aprotic. I recommend drawing the structure of each solvent.
For problem 8.17, all of the reactions will be SN2. For each reaction, identify and evaluate each nucleophile (strong? weak? Strong or weak as a base?) Also, evaluate each solvent as polar protic or polar aprotic. I recommend drawing the structure of each solvent. (d) Sodium cyanide in dimethyl sulfoxide (e) Sodium azide in aqueous ethanol (f) Sodium hydrogen sulfide in ethanol
b) Explain in detail what characteristics of the alkyl halide influence whether a mechanism will be SN1 or SN2. c) Explain in detail what characteristics of a nucleophile influence whether a reaction will be SN1 or SN2.
9) Suppose I want to perform a simple substitution reaction, replacing the OH with a Cl in the following compound. Which of the following reagents works best? Explain (and that means explain why the wrong answers are wrong as well as why the right answer is right). Option A: Addition of HBr Option B: Addition of SOC12/pyridine Option C: Addition of SOCl2 only OH ? J1
Choose the reagent(s) that would be most likely to complete this reaction. I||| / A B C D 1. BH3-THF 2. H2O2, NaOH Br₂ H₂O OsO4 (catalytic) NMO RCO3H Done
Question 4. A) Predict the most likely site of electrophilic aromatic substitution in each compound below. If you think there will be a major and minor product, identify both. Briefly explain the reason(s) that you made your choice. B) Rank the three compounds in increasing order of reactivity (number them as 1,2 and 3 being the most reactive).
6) Complete the following mechanism. (D and SN2) H Br. NaH "H: " 7) Complete the following mechanism. (D and SN2) H NaH "H: " Br. SN2 Good Nucleophile SN2 ether THF
3) Any compound or ion with at least one lone pair can be considered a base and/or a nucleophile. The relative basicity and nucleophilicity of the species is one of the most important factors that determine the mechanism of a reaction on sp³-carbon atoms. Please show an example of a) a reagent that is a strong nucleophile and a strong base, b) a reagent that is a weak nucleophile and a strong base, c) a reagent that is a strong nucleophile and a weak base, d) a reagent that is a weak nucleophile and a weak base. Which nitrogen atom in the structure below is most nucleophilic? Please explain by discussing the electron density around each nitrogen atom. Show at least three resonance structures of the compound. N.
2. For each of the nucleophilic substitution reactions below (a-d), place a box around the most nucleophilic atom, circle the most electrophilic atom, and draw a straight arrow to point to the leaving group. Then predict the main carbon containing product of each reaction, drawing its line structure showing stereochemistry using wedges and dashes, if appropriate. Predict the type of mechanism: circle SN1 or SN2. a. b. C. d. e. Br + Na CEN Br →→ CI + Na N=N=N (NaN3) Za H CI + O-H Sigla Na CH3 (+ + Na S-CH3 water SN2 SN1 SN2 SN1 SN2 SN1 SN2 SN1 SN² SN1
In order to complete the synthesis shown below, you would need to use [ Select ] as the nucleophile source and [Select] as the solvent. H3C OH H3C Br H3CY CH3 H3C CH3
6. Rewrite figure 7.18 (Determining expected mechanisms) with relevant examples for box headers and example for mechanisms in the boxes. Strong base Strong base Weak base Weak base Weak nucleophile Strong nucleophile Strong nucleophile Weak nucleophile 1° E2 E2 SN2 SN2 2° E2 E2 SN2 SN2 XX 3° E2 E2 SN1 SN1 E1
e 2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH3OH