Draw the structures of all isomeric alcohols of molecular formula $C_{5} H_{12} O$ and give their IUPAC names.

Classify the isomers of alcohols in question 3. (i) as primary secondary and tertiary alcohols.

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Solution

(i) Molecular formula $C_{5} H_{12} O$ represents eight isomeric alkanols. These are:

(a) $5 C H_{3} - 4 C H_{2} - 3 C H_{2} - 2 C H_{2} P e n t a n - 1 - o l - 1 C H_{2} - O H$

(b) $4 C H_{3} - 3 C H - 2 C H_{2} - 1 C H_{2} - O H | C H_{3} 3 - m e t h y l b u t a n - 1 - o l$

(c) $C H_{3} | 3 C H_{3} - 2 C - 1 C H_{2} - O H | C H_{3} 2, 2 - D i m e t h y l p r o p a n - 1 - o l$

(d) $4 C H_{3} - 3 C H_{2} - 2 C H - 1 C H_{2} - O H | C H_{3} 2 - m e t h y l b u t a n - 1 - o l$

(e) $5 C H_{3} - 4 C H_{2} - 3 C H_{2} - 2 C H - 1 C H_{3} | O H P e n t a n - 2 - o l$

(f) $4 C H_{3} - 3 C H - 2 C H - 1 C H_{3} | C H_{3} 3 - m e t h y l b u t a n - 2 - o l | O H$

(g)

(h) $5 C H_{3} - 4 C H_{2} - 3 C H - 2 C H_{2} - 1 C H_{3} | O H P e n t a n - 3 - o l$

Primary alcohols: (a), (b), (c) and (d);

Secondary alcohols: (e), (f), and (h)

Tertiary alcohol: (g)

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