An unknown alkyl halide [ X ] reacts with alcoholic KOH and produces a hydrocarbon ( C 4 H 8) as the major product. Ozonolysis of this hydrocarbon affords one mole of propanaldehyde and one mole of formaldehyde. Suggest which organic compound among the following has the correct structure of the above alkyl halide [ X ] ?

Question

An unknown alkyl halide [ X ] reacts with alcoholic KOH and produces a hydrocarbon ( C 4 H 8) as the major product. Ozonolysis of this hydrocarbon affords one mole of propanaldehyde and one mole of formaldehyde. Suggest which organic compound among the following has the correct structure of the above alkyl halide [ X ] ? (A) CH 3 CH 2 CH 2 CH 2 Br (B) CH 3 CH ( Br ) CH 2 CH 3 (C) CH 3 CH ( Br ) CH ( Br ) CH 3 (D) Br ( CH 2)4 Br

Tardigrade Admin · Accepted Answer

As the ozonolysis gives propanaldehyde and formaldehyde thus the hydrocarbon is

1-butene C H_{3} C H_{2} C H = C H_{2} (C_{4} H_{8})

1-butene can be obtained by

C H_{3} - C H_{2} - C H_{2} - C H_{2} - B r A l c . K O H - H B r C H_{3} C H_{2} C H = C H_{2}

.

$C H_{3} C H_{2} C H_{2} C H_{2} B r$

$C H_{3} C H (B r) C H_{2} C H_{3}$

$C H_{3} C H (B r) C H (B r) C H_{3}$

$B r (C H_{2})_{4} B r$

As the ozonolysis gives propanaldehyde and formaldehyde thus the hydrocarbon is $1-butene C H_{3} C H_{2} C H = C H_{2} (C_{4} H_{8})$
1-butene can be obtained by $C H_{3} - C H_{2} - C H_{2} - C H_{2} - B r A l c . K O H - H B r C H_{3} C H_{2} C H = C H_{2}$ .

CH3​CH2​CH2​CH2​Br

CH3​CH(Br)CH2​CH3​

CH3​CH(Br)CH(Br)CH3​

Br(CH2​)4​Br

As the ozonolysis gives propanaldehyde and formaldehyde thus the hydrocarbon is 1-buteneCH3​CH2​CH​=CH2​(C4​H8​) 1-butene can be obtained by CH3​−CH2​−CH2​−CH2​−BrAlc.KOH−HBr​CH3​CH2​CH=CH2​.

$C H_{3} C H_{2} C H_{2} C H_{2} B r$

$C H_{3} C H (B r) C H_{2} C H_{3}$

$C H_{3} C H (B r) C H (B r) C H_{3}$

$B r (C H_{2})_{4} B r$

As the ozonolysis gives propanaldehyde and formaldehyde thus the hydrocarbon is $1-butene C H_{3} C H_{2} C H = C H_{2} (C_{4} H_{8})$
1-butene can be obtained by $C H_{3} - C H_{2} - C H_{2} - C H_{2} - B r A l c . K O H - H B r C H_{3} C H_{2} C H = C H_{2}$ .