Two of the electrophiles in Table 1 cannot be used in the sodium iodide test. Wh

Question

Two of the electrophiles in Table 1 cannot be used in the sodium iodide test. Which two, and why

can’t they be used?

Table 1. List of Electrophiles

1-chlorobutane 1-bromobutane 1-iodobutane

2-chlorobutane 2-bromobutane 2-iodobutane

2-chloro-2-methylpropane 2-bromo-2-methylpropane

Benzyl chloride Bromobenzene

Part II

3

Pre-Lab Assignment: Nucleophilic Substitution Reactions – Relative Rates of Electrophiles

Remove this page from the manual and answer the questions directly on this paper.

Pre-lab questions are to be turned in to your TA as you enter the laboratory.

Name:___________________________________ Lab Section:_____________________

1. Two of the electrophiles in Table 1 cannot be used in the sodium iodide test. Which two, and why

can’t they be used?

2. Of the ten substrates, which would you expect to react fastest in each of the two tests? Which

would you expect to react slowest? Why?

Explanation / Answer

answer : Benzyl chloride , Bromobenzene these two cannot be used in the sodium iodide test

explanation : bromo benzen there will resonance effect is there . so there will be double bond character in between Br and C. so Br+ ion cannot leaves from ring . so it cannot form electrophile.

benzyle chloride also cannot form electrophile with NaI . because I is easy leaving group compared to Br. so I cannot replace Br

answer : Bromobenzene react slowest, 2-bromo-2-methylpropane reacts fastest

explantion :

2-bromo -2-methyl propane forms tertiary carbocation in the reaction . tertiary carbo cation electrophile is stable so react with nucleophile very rapidly

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