Question

9. (20pts) For each pair of molecules, circle the one with the indicated property: a) the better nucleophile in MeCN b) the better nucleophile in CH3OH CH3S or CH30 c) the ion that will give the higher substitution to elimination product ratio CH3S or CH30 Won d) the more reactive alkyl halide in a solvolysis reaction aior e) the more reactive alcohol towards substitution — он оr f) the more reactive alkyl halide in an E2 reaction balt Br g) the reaction that takes place more rapidly CH,Br + HO DMSO CH,OH + Br CH2Br + HO EOH CH3OH + Br h) the compound that shows the larger wavenumber for the C-C stretch in the IR spectrum M i) the more stable radical j) the larger wavenumber of the C=O stretch in the IR spectrum Vivo Cior

Answer 1

A)

2nd one phonoxide is better nucleophile in MeCN ( other have -CN, which is an electron withdrawing group)

B.

Methoxide is better nucleophile as it is conjugate base of poor acid than, conjugate base of methane thiol.

C. First one ,as it is weaker acid or weaker nucleophile.

D. First one, alkyl halide than vinyl one.

E. First one, as in case case of 2nd one substitution will at Cl centre as it is better leaving group.

F. 2nd one, as in E2 least hindered will be more reactive.

G. In DMSO reaction will we faster ,aprotic solvent.

H. In cyclopentane C-C bonds are stronger than cyclopropane , thus 1st will show IR at higher wave number.

I. 2nd one will be more stable radical as in 1st one canon of allyl radical is primary.

J. First one , acyl chloride will show at higher wave number than amide.