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askall 4. Rank each of the following sets of molecules in order of increasing SN

ID: 698065 • Letter: A

Question

askall

4. Rank each of the following sets of molecules in order of increasing SN2 reactivity (9%) [A] CH3CH2C CH3CH2I, CI 5. How could you distinguish between the compounds in each of the following pairs using UV spectroscopy? (9%) and and and CI OCH 6. When compound A (CsH120) is treated with HBr, it forms compound B (CsHnBr). The H NMR spectrum of compound A has one singlet (1), two doublets (3, 6), and two multiplets (both 1) (number in parentheses are the relative areas of the signals). The 'H NMR spectrum of compound B has a singlet (6), a triplet (3), and a quarter (2). Please identify compounds A and B. (896) 7. Using any necessary inorganic reagents, show how you would convert acetylene and isobutyl bromide to the following compounds. (6%) [A] meso-2,7-dimethyl-4,5-octanediol, (CH)CHCH CH(OH)CH OH)CH CH(CH3)h [B] ( 2,7-dimethyl-4,5-octanediol

Explanation / Answer

Ans 4 :

SN2 is nucleophilic substitution bimolecular reaction , which occurs in a single step.

Since the reaction involves simultaneous attack of nucleophile and formation of an intermediate , the steric hinderance plays a major role in defining the reactivity of the reactants.

So here :

A] : C6H11Cl < CH3CH2Cl < CH3CH2I

B] : (CH3)2CHBr < CH3CH2CH2Br < CH3CH2Br < CH3Br

C] (CH3CH2)2CHCH2Br < (CH3)2CHCH2Br < CH3CH2CH2CH2CH2Br