1) Arrange the following in order of decreasing base strength (strongest base fi

Question

1) Arrange the following in order of decreasing base strength (strongest base first) A. CH,CH2O B. NH2 C. CH,CH2 D. H-CEC 2) When an aldehyde is reacted with an alkyl lithium compound, after acid hydrolysis the result is a) a ketone b) a primary alcohol c) a secondary alcohol d) a tertiary alcohol 3) Predict the major product from the reaction sequence below. 1) NaNH2 2) CH3Br 1) NaNH2 2)1-iodobutane | a) 1-nonyne b) 2-nonyne c) 1-octyne d) 2-octyne e none of these 4) Which alkyne below would give two different ketones in approximately the same amount with the H2SO4/Hg2+ catalyzed addition of water? a) cyclodecyne b)4-decyne c) 1-decyne d) 5-decyne

Explanation / Answer

1)

Basic strength is proportional to electron donating tendency

in A, negative charge is on oxygen

in B, negative charge is on Nitrogen

in C, negative charge is on carbon which is sp3 hybridised

in D, negative charge is on carbon which is sp hybridised

electronegativity order is :

O > C in sp > N > C in sp3

Greater electronegativity implies greater electron holding tendency and hence weaker base

So, A will be weakest base and C will be strongest

B will 2nd strongest

Answer: d

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