Rank the relative reactivity of nucleophiles. The shortest time means fastest reaction, which gets number 1 reactivity. The longest time means slowest reaction, which gets number 4.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 36AP
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1-Chlorobutane was treated with different nucleophiles shown in the table. The reaction was carried out
in acetone at 25°C.
CH;CH2CH2C1 + HNu or NaNu
CH3CH2CH,Nu + Precipitate in some reactions
Time until precipitate
Nucleophile
(Nu)Compound
Reaction
Number
observed
Relative reactivity
NaOCH3
0.52 sec
1
НОСНЗ
none observed
2
NaSCH3
0.15 sec
3
HSCH3
4.35 min
4
1. Rank the relative reactivity of nucleophiles. The shortest time means fastest reaction, which gets number 1
reactivity. The longest time means slowest reaction, which gets number 4.
2. The formula of the precipitate that forms in Reaction 3 is
3. Explain why the nucleophile in Reaction 1 is stronger than the nucleophile in Reaction 2.
4. Explain why the nucleophile in Reaction 3 is stronger than the nucleophile in Reaction 1.
Transcribed Image Text:1-Chlorobutane was treated with different nucleophiles shown in the table. The reaction was carried out in acetone at 25°C. CH;CH2CH2C1 + HNu or NaNu CH3CH2CH,Nu + Precipitate in some reactions Time until precipitate Nucleophile (Nu)Compound Reaction Number observed Relative reactivity NaOCH3 0.52 sec 1 НОСНЗ none observed 2 NaSCH3 0.15 sec 3 HSCH3 4.35 min 4 1. Rank the relative reactivity of nucleophiles. The shortest time means fastest reaction, which gets number 1 reactivity. The longest time means slowest reaction, which gets number 4. 2. The formula of the precipitate that forms in Reaction 3 is 3. Explain why the nucleophile in Reaction 1 is stronger than the nucleophile in Reaction 2. 4. Explain why the nucleophile in Reaction 3 is stronger than the nucleophile in Reaction 1.
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