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1. Aldehydes, ketones, and carboxylic acids are important organic functional groups.
2. Aldehydes and ketones can be prepared through oxidation of alcohols or by dehydrogenation. Carboxylic acids can be prepared by oxidation of alcohols or from nitriles.
3. These carbonyl compounds undergo nucleophilic addition and condensation reactions due to the polar carbonyl group. Aldehydes are more reactive than ketones due to less steric hindrance.
Description originale:
aldehyde, ketone and carboxylic acid
Titre original
aldehyde, ketone and carboxylic acid class 12 cbse
1. Aldehydes, ketones, and carboxylic acids are important organic functional groups.
2. Aldehydes and ketones can be prepared through oxidation of alcohols or by dehydrogenation. Carboxylic acids can be prepared by oxidation of alcohols or from nitriles.
3. These carbonyl compounds undergo nucleophilic addition and condensation reactions due to the polar carbonyl group. Aldehydes are more reactive than ketones due to less steric hindrance.
1. Aldehydes, ketones, and carboxylic acids are important organic functional groups.
2. Aldehydes and ketones can be prepared through oxidation of alcohols or by dehydrogenation. Carboxylic acids can be prepared by oxidation of alcohols or from nitriles.
3. These carbonyl compounds undergo nucleophilic addition and condensation reactions due to the polar carbonyl group. Aldehydes are more reactive than ketones due to less steric hindrance.
2 H 5 CHO (Propanal) but CHO gp attached with ring called carbaldehyde (ii) >C= Ketone CH 3 COC 2 H 5 Pentanone C 6 H 5 COC 6 H 5 Benzophenone
(iii) (iv)CH 3 CH 2 COCl Propanoal chloride (v) CH 3 COOC 2 H 5 ethyl ethanoate (vi) CH 3 CH 2 CONH 2 Propanamide, CH 3 CONHCH 3 N-methyl ethanamide (vii) High polarity of carbonyl gp is due to resonance 2. General methods of Preparation of CHO & >C=O (i)By oxidation of 1 0 alcohol form CHO, 2 0 alcohol form >C=O RCH 2 OH ------acidic K 2 Cr 2 O 7 , [O]----> RCHO + H 2 O R 2 CHOH ---[O]------> R 2 =O + H 2 O (ii)By dehydrogenation of alcohol 1 0 form CHO, 2 0 alcohol form >C=O RCH 2 OH -----Cu, 573K-----> RCHO + H 2 R 2 CHO ----Cu,573K----> R 2 C=O + H 2 (iii) Ozonolysis
(iv) From alkyne only ethyne give CHO other give Ketone Ethyne/ butyne + H 2 O CH 3 CHO / CH 3 CH 2 C(O)CH 3 3. Special method for preparation of -CHO (i)Rosenmund Reduction (ii) Stephen Reduction (iii) Etard reaction (iv) Gatterman koch reaction 4. Special method for preparation of ketone (i)From acyl halide
(ii) From Grignard reagent (iii) By friedel craft acylation 5. Physical Properties of CHO, >C=O (i)Only HCHO gas other are liquid or solid (ii) b.p -OH > -CHO > R-O-R > Alkane due to Hydrogen bonding (iii) HCHO, CH 3 CHO, CH 3 COCH 3 are soluble in water other not due to H-bonding 6. Chemical Properties of aldehyde and ketone: - Due to weak and polar nature of C=O nature (i)Nucleophilic addition Reaction: - Nucleophile (:Nu) combine with C=O and convert triangular planner structure to tetrahedral structure then react with H + to form addition product. Addition of HCN, NaHSO 3 , RMgX, OH, NH 3 Aldehyde are more reactive than ketone due to less steric effect (a)With HCN -> (b) With NaHSO 3
The crystalline compound can be converted to original CHO/>C=O Therefore, property used to separate and purify the aldehyde or ketone (c) Grignard reagent: - To obtain higher alcohol (d) Addition of alcohol: - monohydric alcohol form Hemiacetal, ketonketals (e) CH 3 CH=O + NH 2 OH (oxime) CH 3 C=NOH ethanal oxime (CH 3 ) 2 C=O + NH 2 NH 2 (hydrazine) (CH 3 ) 2 =NNH 2 Propanone hydrazine + NH 2 NHC 6 H 5 (phenyl hydrazine) (CH 3 ) 2 C=NNHC 6 H 5 Propanone phenyl hydrazine + NH 2 CONH 2 (Carbazine) (CH 3 ) 2 C=NCONH 2 Propanone semi carbazine (f) Reduction: - aldehyde form 1 0 alcohol ketone form 2 0 alcohol RCHO + H 2 LiAlH 4 ---> RCH 2 OH R 2 C=O + H 2 LiAlH4---> R 2 CHOH Clemmensen reduction: - When aldehyde or Ketone reduce by Zn-Hg amalgam and conc. HCl form alkane Wolff-Kishner reduction: - When aldehyde or ketone reduce by hydrazine and then heat with KOH and glycol form alkane (g) Oxidation: - Aldehyde on mild oxidation with acidic KMnO 4 , K 2 Cr 2 O 7 , HNO 3 , Tollen reagent, Fehling solution form carboxylic acid but ketone cannot easily oxidise [Reaction used to distinguish aldehyde and ketone RCHO + O ----------> RCOOH] Tollen reagent: - It is ammonical silver nitrate AgNO 3 + NH 4 OH AgOH + NH 4 NO 3 AgOH + NH 4 OH [Ag(NH 3 ) 2 ]OH (Tollen reagent) + 2H 2 O RCHO + 2[Ag(NH 3 ) 2 ]OH RCOOH + 2Ag(silver mirror) + 4NH 3 + H 2 O Fehling solution: - (h) Iodoform Test: - When alcohol (CH 3 CH 2 OH), aldehyde or ketone having -CH 3 gp react with NaOH and I 2 form yellow ppt of iodoform CHI 3 CH 3 CH 2 OH + 4I 2 + 6NaOH CHI 3 + HCOONa + 5NaI CH 3 CHO + 3I 2 + NaOH/Na 2 CO 3 CHI 3 + CH 3 COONa + NaI/CO 2 CH 3 COCH 3 + 3I 2 + 4NaOH CHI 3 + CH 3 COONa + 3NaI (i) Aldol condensation: - Aldehyde having at least one -Hydrogen when react with dil. NaOH form hydroxyl aldehyde (Aldol) CH 3 CHO + HCH 2 CHO ---NaOH---> CH 3 CH(OH)CH 2 CHO ---------> CH 3 CH=CHCHO (j) Cross aldol condensation: - When two different aldehyde having -H atom react with NaOH form four type of aldol [CH 3 CHO + CH 3 CH 2 CHO] (i)CH 3 CHO + CH 3 CHO + NaOH CH 3 CH(CHO)CH 2 CHO (ii) CH 3 CH 2 CHO + CH 3 CH 2 CHO CH 3 CH 2 CH(OH)CH(CH 3 )CHO (iii) CH 3 CHO + CH 3 CH 3 CHO CH 3 CH(OH)CH(CH 3 )CHO (iv)CH 3 CH 2 CHO + CH 3 CHO CH 3 CH 2 CH(OH)CH 2 CHO (k) Cannizzaro reaction: - Aldehyde having -H atom react with NaOH form NaOH form Sod. Salt of carboxylic acid and alcohol (l) Electrophilic substitution reaction: - -CHO and >C=O gp are e - withdrawing gp. Therefore, give m product Uses of aldehyde and Ketone: - (i) As solvent (ii) 40% aq. HCHO called formalin used as preservative of biological species. (iii) HCHO in Bakelite, urea formaldehyde glue (iv) C 6 H 5 CHO in perfume industry Carboxylic Acid RCOOH HCOOH Formic acid, methanoic acid CH 3 COOH Acetic acid, Ethanoic acid CH 3 CH 2 CH 2 COOH butyric acid (butter) butanoic acid CH 3 CH 2 CH 2 CH 2 CH 2 COOH (Caproic acid) Capper (goat) Hexanoic Acid In aq. exist as carboxylate ion Preparation of Carboxylic acid:- (i)By oxidation of 1 0 alcohol: - (ii) By oxidation of alkyl benzene (iii) From Nitrile of amide :- Hydrolysis of cyanide or amide RCN/ArCN + H 2 O ----H + /OH - -----> R/ArCONH 2 ----- H + /OH - + H 2 O----> RCOOH/ArCOOH + NH 3 (iv)Form Grignard Reagent (v)From acyhalide or anhydrous acid (vi)By hydrolysis of ester RCOOR + H 2 O ----H + ---> RCOOH + ROH Physical Properties of Carboxylic Acids 1. Upto 9 C atoms liquid and higher solid like wax 2. Boiling point COOH > -OH > -CHO > >C=O > R-O-R > Alkane due to strong H-Bonding. Even in vapour phase exist as dimer. Chemical Properties 1. In aq. acidic due to carboxylate ion Alcohol give H 2 with Na, Phenol react with NaOH, but Carboxylic acid give effervence of CO 2 with NaHCO 3 Acidic Nature FCH 2 COOH > ClCH 2 COOH > BrCH 2 COOH > ICH 2 COOh > CH 3 COOH due to I effect. Cl 3 CCOOH > Cl 2 CHCOOH > ClCH 2 COOH > CH 3 COOH e - withdrawing group increases acidity Ph < I < Br < Cl < F < CN < NO 2 < CF 3 e - repelling group decrease acidity C 2 H 5 COOH < CH 3 COOH < HCOOH 2. On heating with P 2 O 5 /H 2 SO 4 form acid anhydride 3. Esterification RCOOH + ROH ----H + -----> RCOOR + H 2 O 4. Reaction with PCl 5 , PCl 3 , SOCl 2 -------> RCOCl + POCl 3 /H 3 PO 3 /SO 2 + HCl 5. Reaction with NH 3 form amide CH 3 COOH + NH 3 --------> CH 3 CONH 2 + H 2 O 6. Reduction form 1 0 alcohol RCOOH ---------LiAlH 4 /B 2 H 6 ------> RCH 2 OH 7. Decarboxylation :- When sodium salt of carboxylic acid react with sodalime form alkane and Na 2 CO 3 8. Halogenation ( Hell volhard Zelinsky) HVZ reaction When carboxylic acid having -H-atom are halogenated with Cl 2 /Br 2 in presence of Red P4 form -halogenated carboxylic acid. RCH 2 COOH + Cl 2 /Br 2 ---Red P 4 ----> RCXH-COOH [X = Cl 2 , Br 2 ] 9. Electrophilic substitution reaction : give m product 10. Carboxylic acid does not undergoes friedel Craft reaction (i)Since, -COOH gp is deactivating (ii) AlCl 3 e - deficient react with carboxylic gp.