ORGANIC CHEMISTRY XII (ALL) QUESTION BANK ON ACIDITY, BASICITY H-BONDING & TA UTOMERISM IACIDITY. BASICITY. H-BONDING & TAUTOMERISM Q. 1 (a) (b) (c) Write equations show ing the Lewis acid-base reaction that takes place when Methyl alcohol reacts wit h BF3. Methyl chloride reacts with AICI3. Dimethyl ether reacts with BF3. Which of the following are lewis acids & which are lewis bases? CH3 (a) CH 3 CH 2 -N-C H : CH3 (d) :Brf (b) CH 3 -C CH3 *(e) (CH3)3B (C)(C6H5)3P: (f) m ^/C?. 3 ' ,Jb) Jt) Q. 4 (a) (b) (c) (d) (e) (f) (g) Q.5 Which would you expect to be the stronger acid? Explain your reasoning in each i nstance. CH2C1C02H or CHC^CO.H CC13C02H or CHC12C02H CH2FC02H or CH2FCH2C02H Wri te equations for the acid base reaction that would occur when each of the follow ing compounds or solution are mixed. In each case label the stronger acid & stro nger base,& the weaker acid & weaker base. NaH is added to CH3OH NaNH2is added t o CH3CH2OH Gaseous NH3 is added to ethyl lithium in hexane NH4C1 is added to NaN H2 in liq. NH3 (CH3)3CONa is added to H 2 0 NaOH is added to (CH3)3 C-OH C2H5OH is added to a solution of HC = C~Na+ in liquid NHV CHjCHjMgBr + CH3C = CH >A+B Choose the member of each of the following pairs of compunds that is likely to b e the stronger base. v (a) NH 2 or NH3 o( Jb) OH orH 2 0 O J c ) O H or SH 4 Choose the member of each of the following pairs of compunds that is likely to b e the weaker base. 2 H 2 0 or H30 (C) CI", SH v , (b) H2S, HS- S ~ J d ^ F - , OH ~ MTV, CH3 J e ) HF, H 2 0, NH3 , OH- SH", SeH CH, - ^ C H V + lC i r O +CH^-P-H H CH3-O-CH3 CH 3 O II + :O-H>CH3 -O: H CH 3 :o: (c) H - C - H + :NH 3 IS M ->H-C=RH NH 3 2 (d) CH 3 - N H 2 + CH 3 - CH 2 - C I : - > CH 3 - N H 2 - CH 2 CH 3 + : C I : (CH3)3 CC1 + A1C13 JL4 + BR "Or M (e) (f) > (CH3)3