21.9. Draw a structural formula for each compound. (a) 2,3-Dinitrotoluene (b) 3-Propylanisole (e) Diphenylmethanol (d) -Propylphenol (e) p-Nitroaniline (f) Pentabromobenzene (g) p-Xylene (h) 1,2-Dibenzoic acid (i) Benzyl alcohol (i) m-Nitrotoluene (k) 2,6-Dimethylnaphthalene (1) o-Cresol

Give reasons for the following :(i) Phenol is more acidic than methanol.(ii) The C—O—H bond angle in alcohols is slightly less than the tetrahedral angle (190°28′).(iii) (CH3)3C—O—CH3 on reaction with HI gives (CH3)3C—I and CH3—OH as the main products and not (CH3)3C—OH and CH3—I.

II. Draw structures corresponding to the following names: (a) 2,2-Dimethylpropanoyl chloride (b) N-ethylbenzamide (c) 5,5-Dimethylhexanenitrile (d) Benzoic butyric anhydride (e) trans-2-Methylcyclohexanecarboxamide (f) isopropyl formate (g) acetic propionic anhydride (h) tert-Butyl butanoate

Give the chemical tests to distinguish between following pair of compounds : (i) Propanol and propanone (ii) Ethyl acetate and methyl acetate (iii) Benzaldehyde and benzoic acid (iv) Benzaldehyde and acetaldehyde (v) Formic acid and acetic acid (vi) Propanal and propanol (vii) Ethanoic acid and ethylethanoate

The odor of ripe bananas and many other fruits is due to the presence of esters. For example: Banana oil (isopentyl acetate)     (a) Write the name (common or IUPAC) of the ester responsible for the fragrance of the following: pineapple, orange, apple, peach, & lavender     (b) Choose one fragrant from (a) and name the alcohol and the carboxylic acid needed to synthesize this ester.     (c) Show the detailed mechanism of the Fischer Esterification reaction that will be involved in the synthesis of the fragrant you have chosen in part (a).

Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) aniline

(a) How will you convert:(i) Benzene to acetophenone                 (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.

Give reasons:  (i) Bond length of C = O in carboxylic acids is slightly larger than C = O bond length in carbonyl compounds.  (ii) There are two –NH2 groups in semicarbazide. However, only one –NH2 group is involved in the formation of semicarbazones.  (iii) Benzoic acid is less soluble in water than acetic acid. (iv) Formic acid is a stronger acid than acetic acid.

Please draw the skeletal formula of the following compounds: (A) Isobutyraldehyde (B) α-Ethyl-γ-methoxycaproaldehyde   (C) 6-Hydroxyhexanal (D) 2,4-Pentanedione (E)3-Cyano-7-oxoheptanoic acid

How would you obtain(i) Picric acid (2, 4, 6-trinitrophenol) from phenol,(ii) 2-Methylpropene from 2-methylpropanol?