Haloalkane (Alkyl halide)

Some Important Questions

A. Haloalkane

1. Draw the structure and give IUPAC name of
   a. n-Pentyl chloride b. neo-Pentyl chloride c. tert-Butyl chloride d. tert-Pentyl chloride e. Iso-butyl bromide f. Iso-pentyl iodide g. Iso-hexyl bromide h. Sec-butyl bromide
   i. Methylene chloride j. Ethylidene bromide k. Ethylene bromide l. Propylidene iodide

2. Identify A and B.

Isobutane\ \xrightarrow[h\nu]{Cl_{2}}\ A+B

3. Explain:
   a. 1-chloropropane is not soluble in water.
   b. n-Propyl chloride is liquid but n-butane is a gas.
   c. Ethyl chloride is a gas but ethyl iodide is a liquid.
   d. Tert-butyl chloride has lower boiling point than n-butyl chloride.
4. Write all possible monobromo derivatives of pentane and arrange them in decreasing order of boiling point.
5. Convert ethyl alcohol into a. ethyl methyl ether b. propanoic acid c. n-propyl amine
6. Identify A₁, A₂ and A₃ in the given reaction.

i.\ CH_{3}CH_{2}OH \xrightarrow[]{PCl_{3}}A_{1}\xrightarrow[]{alc.\ NaCN} A_{2}\xrightarrow[]{Na/C_{2}H_{5}OH} A_{3}\\ i.\ CH_{3}CH_{2}OH \xrightarrow[]{PCl_{5}}A_{1}\xrightarrow[]{alc.\ NaCN} A_{2}\xrightarrow[]{Na/C_{2}H_{5}OH} A_{3}

7. Write the structure of all alkenes obtained on heating following alkyl halides with alc. KOH.
   a. 1-chloropentane b. 2-chloropentane c. 3-chloropentane d. 2-chloro 2-methyl butane
8. Convert: a. 1-bromopropane to 2-bromopropane and vice-versa.
   b. 1-chloropropane to 2-chloropropane and vice-versa.
9. Write any three methods of preparation of iodoethane. Starting from Iodoethane, how would you get:
   a. Ethane b. Ethene c. Ethyne d. Butane e. Bromoethane f. Methoxy ethane g. Ethoxy ethane h. Nitroethane i. Ethyl nitrite j. Ethyl carbylamine k. Propanoic acid l. Propanamide m. Ethanol n. 1-amino propane o. N-methyl ethanamine p. But-1-ene

10. Give an example of
    a. Markonikov’s addition b. Peroxide effect c. Dargen’s reaction d. Groove’s process e. Williamson synthesis f. Hofmann’s ammonolysis g. Dehydrohalogenation h. Wurtz reaction i. Kharash effect
11. Write the difference between SN¹ and SN² reaction.
12. What happens when 2-Iodopropane is reacted with sodium in presence of dry ether?

B. Chloroform

1. Give the reaction of preparation of trichloromethane from
   a. Ethanol b. Acetone
2. Starting from chloroform, how could you prepare
   a. Methane b. Ethyne c. Phosgene d. Chloretone d. Chloropicrin e. Chloretone f. Formic acid g. Salicyaldehyde
3. Give reasons:
   a. 1% ethanol is added to bottles containing chloroform
   b. Chloroform is stored in dark brown bottles.
   c. Old chloroform gives white ppt. with AgNO₃.
4. Give an example of
   a. Carbylamine reaction
   b. Reimer-Tiemann reaction