Experiment 20 - Reactivity of various alkyl halides in Snl and Sn2 - Notes. CI C

Question

Experiment 20 - Reactivity of various alkyl halides in Snl and Sn2 - Notes. CI Cl 1) 2) 3) 4) Br Cl 5) 8) 9) 10) 2. List the halides tested in reactivity order in both the Snl and Sn2. 3. Comparing the primary halides 3) and 4), was there a difference in reactivity in the Sn2? If so, why? 4. Comparing the secondary bromides 2), 9), and 10), was there a difference in reactivity in the Sn2? If so, why? [consider the 3-D structures of the secondary bromides 2), 9), and 10), and think about the ease of "backside attack". Making a model may help in visualization.]. 5. Explain the difference in reactivity of alkyl chlorides 1), 3), and 5) in the Sn1 reaction 6. You might not observe a significant difference in the reactivity of the secondary bromides 2), 9), and 10) in the Sni reaction (due to the inexact measurements of the experiment). However, if you do, how would you account for this difference? [think about the geometry of a secondary carbocation] 7. Why did halide 8) not react in either the Snl or Sn2?

Explanation / Answer

q1) Secondary chloride (1) secondary bromide (2),primary chloride (3), primary bromide(4),tertiary bromide (5) phenylbromide (8), cyclohexyl bromide (9)cyclopentyl bromide(10)

SN1 and Sn2 reaction reactivity based on nature of leaving group

SN1 and SN2 reaction recactivity increases with increases laving group nature

R- I >R- Br >R- Cl > F

Increasing order of SN2

Tertiary < secondary <Primary

Compound 5<10<9<1<2<3<4 increasing order of SN2

compound 3<4<1<2<10<9<5 increasing order of SN1

(q3) Butyl bromide(4) more reactive thane butyl chloride(3) due to bromide is best leaving group than chloride

(q4) bromo compound 2,9,10 it will under go SN2 and SN1 reactions based on solvent

If solvent is polar protic solvent favored SN1

If solvent is polar aprotic solvent favored SN2

Order of reactivity 10<9<2

(Q5) Increasing order of SN1

Primary < secondary< Tertiary

Tertiary chloride(5) more reactive than secondary chloride(1) and primary chloride(3) due to tertiary carbocation is more stable compare with secondary and primary carbocation

(Q6) bromo compound 2,9,10 it will under go SN2 and SN1 reactions based on solvent

If solvent is polar protic solvent favored SN1

Order of reactivity 10<9<2

Stability of corbocations order is 10<9<2

(q7) phenyl bromide dose not undergo SN1 SN2 reaction due to bromide attached at double bonded carbon and C-Br bond having shorter and high strength   

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