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Section 1.1 Section 1.2 Section 1.3 - The Student Room

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SECTION 14<br />

5 a i Reagents and condition: treat with a nitrating<br />

mixture (conc. HNO 3<br />

and conc. H 2<br />

SO 4<br />

); keep<br />

temperature below 55 °C.<br />

ii Product: Br<br />

iv<br />

H<br />

C<br />

O<br />

OH<br />

+ CH 3<br />

OH<br />

Br<br />

iii Reactant: CH 3<br />

Cl (or CH 4<br />

)<br />

iv Reactant: CH 3<br />

–CH 2<br />

–CH 2<br />

–X<br />

(X = Cl, Br, I)<br />

v Products:<br />

O<br />

O<br />

HO C<br />

C OH<br />

vi Products:<br />

O<br />

CH 2 CH 2<br />

+ HCl<br />

CH 3<br />

+ 2HCl<br />

v<br />

H<br />

H<br />

H<br />

O<br />

C<br />

+ H 2 O<br />

O CH 3<br />

H<br />

C C + H 2 CH 3 CH 3<br />

H<br />

b<br />

6 a i<br />

b<br />

C<br />

CH<br />

i Electrophilic substitution<br />

ii Electrophilic addition<br />

iii Radical substitution<br />

iv Nucleophilic substitution<br />

v Nucleophilic substitution<br />

vi Electrophilic substitution<br />

ii<br />

iii<br />

iv<br />

v<br />

COO – Na +<br />

CH 2 CH 3<br />

+ H 2 O<br />

CH 3 COO – Na + + NH 2<br />

+ H 2 O<br />

CH 3 CH 2 OH<br />

i Acid–base<br />

ii Hydrolysis<br />

iii Dehydration<br />

iv Esterification<br />

v Reduction<br />

+ 3H 2<br />

Pt<br />

c Examples may be:<br />

i CH 3 COOH + NaOH<br />

ii<br />

iii<br />

CH 3<br />

C NH CH 3<br />

O<br />

Al 2 O 3<br />

CH 3 CH 2 OH CH 2 CH 2 + H 2 O<br />

+<br />

CH 3 COO – Na + + CH 3 NH 2<br />

CH 3 COO – Na + + H 2 O<br />

NaOH<br />

7 a React with hydrogen in presence of finely divided<br />

nickel at 150 °C and 5 atm.<br />

CH 3 CH 2 CH CH CH 2 COOH + H 2<br />

CH 3 CH 2 CH 2 CH 2 CH 2 COOH<br />

b Treat with a solution of HBr in a polar solvent at<br />

room temperature.<br />

CH 3 CH 2 CH CH CH 2 COOH HBr<br />

Br<br />

CH 3 CH 2 CH CH 2<br />

(+ isomer)<br />

Br<br />

CH 2<br />

+<br />

CH 3 CH 2 CH CH 2 CH 2 COOH<br />

(prepared as in b)<br />

OH<br />

CH 3 CH 2 CH<br />

<strong>The</strong>n acidify with dilute acid.<br />

OH<br />

OH<br />

COOH<br />

c Hydrolyse by refluxing with a dilute aqueous solution<br />

of NaOH.<br />

2NaOH<br />

CH 2 CH COO – Na + 2<br />

+ NaBr + H 2 O<br />

CH 3 CH 2 CH CH 2 CH 2 COO – Na + + HCl<br />

CH3 CH 2 CH CH 2 CH 2 COOH + NaCl<br />

+<br />

206

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