An organic compound A with molecular formula
CgH1602 was hydrlysed with dil. H2SO4 to give
carboxylic acid B and alcohol C. Oxidation of C
with chromic acid also produced B. On
dehydration C gives but-1-ene. Identify A
Answers
Answer:
Organic compound A is an ester as on acid hydrolysis it gives a mixture of an acid and an alcohol.
Oxidation of alcohol (C) gives acid (B). Hence, the number of carbon atoms in (B) and (C) are same.
Ester (compound A) has eight C atoms. Hence, both carboxylic acid B and alcohol C must contain 4 C atoms each.
Dehydration of alcohol C gives but-1-ene. Hence, C must be a straight chain alcohol, i.e butan-1-ol
Oxidation of (C) gives (B). Hence, (B) is butanoic acid.
CH
3
CH
2
CH
2
COOCH
2
CH
2
CH
2
CH
3
dilH
2
SO
4
hydrolysis
CH
3
CH
2
CH
2
COOH+CH
3
CH
2
CH
2
CH
2
OH
CH
3
CH
2
CH
2
CH
2
OH
Dehydration
CH
3
CH
2
CH=CH
2
CH
3
CH
2
CH
2
CH
2
OH
CrO
3
/CH
3
COOH
Oxidation
CH
3
CH
2
CH
2
COOHOrganic compound A is an ester as on acid hydrolysis it gives a mixture of an acid and an alcohol.
Oxidation of alcohol (C) gives acid (B). Hence, the number of carbon atoms in (B) and (C) are same.
Ester (compound A) has eight C atoms. Hence, both carboxylic acid B and alcohol C must contain 4 C atoms each.
Dehydration of alcohol C gives but-1-ene. Hence, C must be a straight chain alcohol, i.e butan-1-ol
Oxidation of (C) gives (B). Hence, (B) is butanoic acid.
CH
3
CH
2
CH
2
COOCH
2
CH
2
CH
2
CH
3
dilH
2
SO
4
hydrolysis
CH
3
CH
2
CH
2
COOH+CH
3
CH
2
CH
2
CH
2
OH
CH
3
CH
2
CH
2
CH
2
OH
Dehydration
CH
3
CH
2
CH=CH
2
CH
3
CH
2
CH
2
CH
2
OH
CrO
3
/CH
3
COOH
Oxidation
CH
3
CH
2
CH
2
COOH
Explanation: