1.

Arrange the following in the decreasing order of acidity : (i) (1) n-Butanol (2) Methy1 alcohol (3) sec-Butanol (4) rert-Butanol (ii) (1) HCOOH (2) CH_3 COOH (3) C_2H_5COOH (4) C_6H_5 COOH (5) (CH_3)_2CHCOOH (6) CH_2 C1COOH (iii) (1) CH_3 CH_2CH_2COOH (2) CH_3 CH_2 CHC1COOH (3) CH_3 CHC1CH_2COOH (4) CH_2 C1CH_2 CH_2 COOH (iv) (1) CH_3COOH (2) CH_2C1COOH (3) CHC1_2 COOH (4) C C1_3 COOH (v) (1) CH_3BrCOOH (2) CH_2C1COOH (3) CH_2 FCOOH (4) CH_2 ICOOH (vi) (1) C_6H_5 COOH (2) p-OHC_6 H_4COOH (3) p-CH_3C_6H_4COOH (4) p-C1C_6H_4COOH (5) p-Br C_6H_4COOH (6) p-BO_2C_6 H_4 COOH (vii) (1) o-Hydroxybenzoic acid (2) p-Hydroxybenzoic acid (3) 2,6-Dihydroxybenzoic acid. (viii) (1) HCOOH (2) C_6 H_5 COOH (3) C_6H_5OH (4) HC1 (ix) RCOOH (2) ROH (3) RH (4) NH_3 (5) HOH (6) CH -= CH (x) (1) Phenol (2) p-Chlorophenol (3) p-Nitrophenol (4) m-Cresol (xi) (1) Phenol (2) m-Chlorophenol (3) m-Nitrophenol (4) m-Cresol (xii) (1) Phenol (2) Benzoic acid (3) p-Nitrophenol (4) Carbonic acid (xiii) (1) Phenol (2) Benzyl alcohol (3) Benzene sulphonic acid (4) Benzoic acid (xiv) (1) Phenol (2) p-Chlorophenol (3) 2,4,-Dichlorophenol (4) 2,4,6-Trichlorophenol (xv) (1) Nitroform HC(NO_2)_3 (2) Cyanoform HC(CN)_3 (3) CHC1_3 (xvi) (1) CH_3 SO_2CH_3 (2) CH_3NO_2 (xvii) (1) CH_3 BO - O^(Ө) (2) CH_3CHO (3) CH_3 COOR.

Answer»

Solution :(i)
(ii) `6 gt 1 gt 4 gt 2 gt 3 gt 5` (In `(6) -I` effect of `C1 gt (1)` (standard) `gt (4)+R gt -I` of `PH gt (2) + I`effect of `Me gt (3) + I` effect of `Et gt (5) + I` effect of two `Me` groups) .
(iii) `2 gt 3 gt 4 gt1` (2) `- I` effect of `C1` at `alpha-C gt (3) - I` effect of `C1` at `beta - C gt (4) - I` effect of `C1` at `gamma-C gt (1) + I` effect of `CH_3 CH_2 CH_2`.
(iv) `4 gt 3 gt 2 gt 1`(4) `-I` effect of `3 C1` at `alpha-C gt` (2) `-I` effect of `1 C1` at `alpha-C gt (1) + I` effect of `(CH_3 - )` group
(v) `3 gt 2 gt 1 gt 4 ` (3) `- I` effect of `F = (2) - I` effect of `C1 gt (1) - I` effect of `Br gt (4) - I` effect of `I`
(vi) `6 gt 4 gt 5 gt 1 gt 3 gt 2` (6) `-1` and `-R` effect of `(-NO_2)` group `gt (4) - I` effect of `C1 gt (5) - I` effect of `Br gt (1)` standard `gt (3) + I` and `H.C` effect of `CH_3- at p- gt`
(2) `- I` and `-R` effect of `OH` group at `p-` However, the net effect is more `overline e-`donating than the net effect of `(3)`, since `+R gt + I` and `H.C` effects.
(vii) `3 gt 1 gt 2` (3) Intramolecular H-bonding from two sides `gt (I)` Intramolecular H-bonding from one sides `gt (2) - I` and `+R` effects of `OH` group at `p-`position , net effect is `overline e-`donating.
(viii) `4 gt 1 gt 2 gt 3` (4) Inorganic acid `gt (1)` FORMIC acid (standard) `gt (2)` Benzonic acid, `- I` and `+R` of `Ph` group, net `overline e-`donating `gt (3)` Phenol.
(ix) `1 gt 5 gt 2 gt 6 gt 4 gt 3 gt ` (I) Acid `gt (5) H_2 O gt (2)` Alcohol `gt (6) HC -= CH`
(sp character) `gt (4) nH_3 gt (3)` Alkane (`sp^3` character)
(x) `3 gt 2 gt 1 gt 4` (3) `- NO_2(- I` and `-R` effects of `C1` at `p-) gt(2) - C1 - I` effects of `C1` at `p- gt (1)` Standard (phenol) `gt(4) CH_3 + I` effected of `CH_3` at `m-`position.
(xi) `3 gt 2 gt 1 gt 4`(3) `(-NO_2)` (only `-I` effect of `(-NO_2)` at `m-) gt (2) - C1(-I` effected of `C1` at `m-) gt (1)` Standard (phenol) gt
`(4) Ch_3` (only `+1` effect of `CH_3` at `m-`position.
(xi) `2 gt 4 gt 3 gt 1` (2) Benzoic acid `gt (4)` Weak inorganic acid `gt (3)` Nitro phenol `(-NO_2) (-I` and `-R` effect of `(-NO_2)` at `p- ) gt (1)` phenol.
(xiii) `3 gt 4 gt 1 gt 2` (3) Sulphonic acid, `-I` and `-R` effects of `(-SO_3 H)` group `gt (4)`, Benzoic acid, `- I` and `-R` effects of `(-COOH)` group, but `(-SO_3 H)` effect `gt (-COOH)` effect `gt (1) `Phenol `gt (2)` Alcohol)
(xiv) `4 gt 3 gt 2 gt 1` (4) `- I` effect of `3 C1 gt (3) - I` effect of `2 C1 gt (2) - I` effect of `1 C1 gt (1)` Phenol, standard
(xv) `1 gt 2 gt 3` (1) `-I` effect of three `NO_2` groups `gt (2) - I` effects of three `CN` groups `gt (3) - I` effect of three `C1` groups , ` - I` effect of : `-NO_2 gt - CN gt - C1`.
(xvi) ` 2 gt 1 (2) -NO_2 (-I` effect of `NO_2 ) gt (1) - I` effect `SO_2` and `+ I` effect of two `CH_3` groups.
(xvii) `1 gt 2 gt 3` (1) `-I` effect of `-NO_2 gt (2) -I` effect of `- CHO gt (3) - I` effect of `(- COOR)` group) , `-I` effect of : `- NO_2 gt -CHO gt -COOR`.


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