Advertisements
Advertisements
Questions
An organic compound (A) (molecular formula C8H16O2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid produced (B). (C) on dehydration gives but-1-ene. Write equations for the reactions involved.
An organic compound (A) (molecular formula C8H16O2) was hydrolysed with dilute sulphuric acid to get a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid produced (B). (C) on dehydration gives But-1- ene. Identify (A), (B) and (C) and write chemical equations for the reactions involved.
Advertisements
Solution
- An organic compound A with molecular formula C8H16O2 gives a carboxylic acid (B) and an alcohol (C) on hydrolysis with dilute sulphuric acid. Thus, compound A must be an ester.
- Further, alcohol C gives acid B on oxidation with chromic acid. Thus, B and C must contain an equal number of carbon atoms. Since compound A contains a total of 8 carbon atoms, each of B and C contains 4 carbon atoms.
- Again, on dehydration, alcohol C gives but-1-ene. Therefore, C is of straight chain, and hence, it is butan-1-ol. On oxidation, Butan-1-ol gives butanoic acid. Hence, acid B is butanoic acid.
Hence, the ester with molecular formula C8H16O2 is butylbutanoate.
All the given reactions can be explained by the following equations:
\[\ce{\underset{\underset{(A)}{Butyl butanoate [C8H16O2]}}{CH3CH2CH2COOCH2CH2CH2CH3} + H3O+ ->\underset{\underset{(B)}{Butanoic acid}}{CH3CH2CH2COOH} + \underset{\underset{(C)}{Butanol}}{CH3CH2CH2CH2OH}}\]
\[\ce{\underset{\underset{(C)}{Butanol}}{CH3CH2CH2CH2OH}->[{[O]} Oxidation][Chromic acid (H2CrO4)]\underset{\underset{(B)}{Butanoic acid}}{CH3CH2CH2COOH}}\]
\[\ce{\underset{\underset{(C)}{Butanol}}{CH3CH2CH2CH2OH}->[Dehydration][-H2O]\underset{But-1-ene}{CH3CH2CH=CH2}}\]
APPEARS IN
RELATED QUESTIONS
Identify ‘A' and ‘B’ in the following reaction :
C6H5MgBr + C02 `(`> ‘A’ `(PCl_5)/()`> ‘B’
Write the structures of A and B in the following reactions
Name the reagents used in the following reactions:
Show how the following compound can be converted to benzoic acid.
Ethylbenzene
Show how the following compound can be converted to benzoic acid.
Acetophenone
Show how the following compound can be converted to benzoic acid.
Bromobenzene
Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagent.
Tollens’ reagent
How will you prepare the given compound from benzene? You may use any inorganic reagent and any organic reagent having not more than one carbon atom.
m-Nitrobenzoic acid
How will you prepare the given compound from benzene? You may use any inorganic reagent and any organic reagent having not more than one carbon atom.
p-Nitrobenzoic acid
How will you prepare the given compound from benzene? You may use any inorganic reagent and any organic reagent having not more than one carbon atom.
Phenylacetic acid
The reagent which does not react with both, acetone and benzaldehyde.
Which is the most suitable reagent for the following conversion?
\[\begin{array}{cc}
\phantom{....................}\ce{O}\phantom{.....................................}\ce{O}\phantom{.}\\
\phantom{....................}||\phantom{......................................}||\phantom{.}\\
\phantom{}\ce{CH3 - CH = CH - CH2 - C - CH3 -> CH3 - CH = CH - CH2 - C - OH}\phantom{.}
\end{array}\]
Match the reactions given in Column I with the suitable reagents given in Column II.
| Column I (Reactions) |
Column II (Reagents) |
| (i) Benzophenone Diphenylmethane | (a) \[\ce{LiAlH4}\] |
| (ii) Benzaldehyde 1-Phenylethanol | (b) \[\ce{DIBAL-H}\] |
| (iii) Cyclohexanone Cyclohexanol | (c) \[\ce{Zn(Hg)/Conc. HCl}\] |
| (iv) Phenyl benzoate Benzaldehyde | (d) \[\ce{CH3MgBr}\] |
Assertion: Aldehydes and ketones, both react with Tollen’s reagent to form silver mirror.
Reason: Both, aldehydes and ketones contain a carbonyl group.
Substitution of one alkyl group by replacing hydrogen of primary amines
Which of the following substance produced acetaldehyde on dry distillation?
Match List - I with List - II.
| List - I | List - II | ||
| (a) |  \[\ce{->[CO,HCl][Anhyd. AlCl3/CuCl]}\] |
(i) | Hell-Volhard-Zelinsky reaction |
| (b) |
\[\begin{array}{cc}
\ce{O}\phantom{.................}\\ ||\phantom{.................}\\ \ce{R - C - CH3 + NaOX ->} \end{array}\] |
(ii) | Gattermann-Koch reaction |
| (c) | \[\ce{R - CH2 - OH + R'COOH ->[Conc. H2SO4]}\] | (iii) | Haloform reaction |
| (d) | \[\ce{R - CH2COOH ->[(i) X2/Red P][(ii) H2O]}\] | (iv) | Esterification |
Choose the correct answer from the options given below.
The end product Y in the sequence of reaction:
\[\ce{RX ->[CN^-] X ->[NaOH] Y}\] is:
Hex-4-ene-2-ol on treatment with PCC gives 'A'. 'A' on reaction with sodium hypoiodite gives 'B', which on further heating with soda lime gives 'C. The compound 'C' is ______.
