JAWAHAR NAVODAYA VIDYALAYA RATIBAD BHOPAL

UNIT 12-ALDEHYDE KETONE AND CARBOXYLIC ACID

NOMENCLATURE

(1) Draw the structure of

i. 4-chloropentan-2-one.  (iii) 2-methylbutanal. (iv) 3-methylpentanal.

ii. p-Methylbenzaldehyde (v) 1-phenyl Propan-1-one

(2) Write the name of 

NAME REACTION

(1) Rosenmund reduction (02) Wolf kishner reduction (03) Etard reaction

(4) Aldol condensation (05) Cross aldol condensation (06) Ozonolysis

(7) Cannizzaro's reaction (08) Clemmensen reduction (09)   Decrboxylation

(10) Gatterman koach reaction (11) Kolbe reaction (12) Easterification

(13) Hell volhard zelinsky (HVZ)

CONVERSION

(1) Acetophenone to Benzoic acid (08) Benzoic acid to Benzaldehyde

(2) Benzoic acid from ethylbenzene (09) But-2-enal from ethanol

(3) Benzyl chloride to phenyl ethanoic acid (10) Butanoic acid from butanol

(4) Ethanoic acid to 2-Hydroxyethanoic acid (11) Propanone to propene

(5) Ethyne to Ethanal (12) Benzaldehyde from Phenol

(6) Benzaldehyde from toluene (13) Ethanol to acetone

(7) Benzene to acetophenone

REASONING

(1) Cl–CH2COOH is a stronger acid than CH3COOH. Why?

(2) Carboxylic acids do not give reactions of carbonyl group. Why?

(3) HCHO is more reactive than CH3–CHO towards addition of HCN. Why?

(4) pKa of NO2–CH2–COOH is lower than that of CH3–COOH. Why?

(5) The boiling points of aldehydes and ketones are lower than of the corresponding acids. Why?

(6) What is Tollens’ reagent? Write one usefulness of this reagent.

(7) Write the composition of Fehling solution?

(8) Aldehydes are more reactive than ketones towards nucleophilic reagents.

(9) Aldehydes and Ketones have lower boiling points than corresponding alcohols. Why?

DISTINGUISH

(1) Benzoic acid & ethyl benzoate (07) Benzaldehyde & acetophenone

(2) Benzoic acid & Phenol (08) Propanal & Propanone

(3) Butanal & Butan-2-one (09) Pentan-2-one & Pentan-3-one

(4) Ethanal and Propanal (10) Benzaldehyde & benzophenone

(5) Propanal and butanone (11) Benzaldehyde & benzoic acid

(6) Out of CH3CH2–CO–CH2–CH3 and CH3CH2–CH2–CO–CH3, which gives iodoform test?

COMPLETE FOLLOWING EQUATION

(1) Write the products formed when CH3CHO reacts with the following reagents

(i) HCN (ii) H2N-OH (iii) CH3CHO in the presence of dilute NaOH

(2) Write the structures of the products when Butan-2-ol reacts with the following:

(3) (i) CrO3 (ii) SOCl2

BRAIN STORMING QUESTION

1. An organic compound A, having the formula, C3H8O, on treatment with copper at 573 K, gives B. B does not reduce Fehling’s solution but gives a yellow precipitate of the compound C with I2/NaOH. Deduce the structure of A, B and C.

2. An organic compound (A) which has characteristic odour, on treatment with NaOH forms two compounds (B) and (C). Compound (B) has the molecular formula C7H8O which on oxidation with CrO3 gives back compound (A). Compound (C) is the sodium salt of the acid. Compound (C) when heated with soda lime yields an aromatic hydrocarbon (D). Deduce the structures of (A), (B), (C) and (D). Write chemical equations for all reactions taking place.

3. An organic compound with molecular formula C9H10O forms 2,4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizzaro’s reaction. On vigorous oxidation it gives 1,2-benzenedicarboxylic acid. Identify the compound.

4. An organic compound (A) with molecular formula C8H8O forms an orange red precipitate with 2, 4-DNP reagent and gives yellow precipitate on heating with I2 and NaOH. It neither reduces Tollens’ reagent nor Fehling’s reagent, nor does it decolourise bromine water or Baeyer’s reagent. On drastic oxidation with chromic acid, it gives a carboxylic acid (B) having molecular formula C7H6O2. Identify the compounds (A) and (B) and explain the reactions involved.

5. An organic compound with molecular formula C5H10O does not reduce Tollens’ reagent but forms an addition compound with sodium hydrogen sulphite and gives a positive iodoform test. On vigorous oxidation, it gives ethanoic acid and propanoic acid. Identify the compound and write all chemical equations for the reactions.

6. An organic compound A has the molecular formula C8H16O2. It gets hydrolysed with dilute sulphuric acid and gives a carboxylic acid B and an alcohol C. Oxidation of C with chromic acid also produced B. C on dehydration reaction gives but-1-ene. Write equations for the reactions involved.

7. An organic compound with molecular formula C9H10O forms 2,4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizzaro’s reaction. On vigorous oxidation it gives 1,2-benzene-di-carboxylic acid. Identify the compound.

8. A ketone A(C4H8O), which undergoes a haloform reaction gives compound B on reduction. B on heating with sulphuric acid gives a compound C which forms monozonide D. D on hydrolysis in presence of zinc dust gives only acetaldehyde E. Identify A, B, C, D and E. Write the reactions involved.

An organic compound A(C3H6O) is resistant to oxidation but forms compound B(C3H8O) on reduction. B reacts with HBr to form the compound C. C with Mg forms Grignard reagent D which reacts with A to form a product which on hydrolysis gives E. Identify A and E.