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Published on: 07/01/2020
Carbonyl Compounds
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1.
Which of the following acids do not exhibit optical isomerism?
lactic acid
tartaric acid
maleic acid
both (a) and (b)
2.
Which among the following on oxidation with alk.KMnO4 will give butanone?
Butan -1- ol
Butan - 2-ol
Both (a) and (b)
Neither (a) nor (b)
3.
Which one of the following reduces tollens reagent
formic acid
acetic acid
benzophenone
none of these
4.
In the following reaction, \(HC\equiv CH \overset { { H }_{ 2 }{ SO }_{ 4 } }{ \underset { HgS{ O }_{ 4 } }{ \longrightarrow } } X\) Product ‘X’ will not give _______.
Tollen’s test
Victor meyer test
Iodoform test
Fehling solution test
5.
Assertion: 2,2 – dimethyl propanoic acid does not give HVZ reaction.
Reason: 2 – 2, dimethyl propanoic acid does not have \(\alpha\) - hydrogen atom
Codes:
A) if both assertion and reason are true and reason is the correct explanation of assertion.
B) if both assertion and reason are true but reason is not the correct explanation of assertion.
C) assertion is true but reason is false
D) both assertion and reason are false
if both assertion and reason are true and reason is the correct explanation of assertion.
if both assertion and reason are true but reason is not the correct explanation of assertion.
assertion is true but reason is false
both assertion and reason are false
6.
Benzaldehyde reduces Tollen's reagent but not Fehling's solution explain.
7.
Arrange the following in increasing order of reactivity towards nucleophilic addition HCHO CH3CHO and CH3COCH3
8.
What happens when calcium acetate is dry distilled?
9.
What is angle of deviation due to reflection?
10.
A carbonyl compound A having molecular formula C5H10O forms crystalline precipitate with sodium bisulphate and gives positive iodoform test. A does not reduce Fehling solution. Identify A.
11.
Identify X and Y.
\({ CH }_{ 3 }CO{ CH }_{ 2 }{ CH }_{ 2 }COO{ C }_{ 2 }{ H }_{ 5 }\overset { { CH }_{ 3 }MgBr }{ \longrightarrow } X\overset { { H }_{ 3 }{ O }^{ + } }{ \longrightarrow } Y\)
12.
An organic compound A (C7H6O) forms a bisulphite. A when treated with alcoholic KCN forms B (C14H12O2) and A on refluxing with sodium acetate and acetic anhydride forms an add C (C9HsO2). Identify A, B and C. Explain the conversion of A to B and C.
13.
Explain why carboxylic acids behave as acids. Discuss briefly the effects of electron withdrawing and donating substituents on acid strength of carboxylic acids.
14.
An alkene (A) on ozonolysis gives propanone and aldehyde (B). When (B) is oxidised (C) is obtained. (C) is treated with Br2/P gives (D) which on hydrolysis gives (E). When propanone is treated with HCN followed by hydrolysis gives (E). Identify A, B, C, D and E.
15.
How is carboxylic acid prepared from alcohols?
16.
Formaldehyde and benzaldehyde give Cannizaro reaction but acetaldehyde does not - account for this.
17.
How is acetaldehyde prepared by the ozonolysis of CH3CH=CHCH3?
18.
Complete the following reaction
\({ CH }_{ 3 }-{ CH }_{ 2 }-{ CH }_{ 2 }-\underset { \overset { || }{ O } }{ C } -{ CH }_{ 3 }\overset { HO-{ CH }_{ 2 }-{ CH }_{ 2 }-OH }{ \underset { { dry }{ HCl} }{ \longrightarrow } } ?\)
19.
Write the structure of the major product of the aldol condensation of benzaldehyde with acetone.
1.
(c)
maleic acid
2.
(b)
Butan - 2-ol
3.
4.
5.
A) if both assertion and reason are true and reason is the correct explanation of assertion.
6.
Benzaldehyde reduces Tollen's reagent, but does not reduce Fehling's solution. Because Ag+ is more easily reduced to Ag than Cu2+ to Cu+
7.
The order of reactivity of aliphatic carbonyl compounds towards the nudeophilic addition reaction is, HCHO > CH3CHO > CH3COCH3
8.
When calcium acetate is dry distilled, acetone is formed.
9.
The angle between the incident and deviated light ray is called angle of deviation of the light ray.
10.
An carbonyl compound having molecular formula C5H10O giving positive iodoform test. It does not reduce Fehling solution.So it is 2- pentanone.
∴ (A) is 2-pentanone.
11.
12.
(i) An organic compound (A) with formula C7H6O form bisulphite means it must be benzaldehyde C6H5CHO.
(ii) Benzaldehyde on treatment with KCN form benzoin.
\(\underset { (A) }{ { C }_{ 6 }{ H }_{ 5 }CHO+{ C }_{ 6 }{ H }_{ 5 }CHO } \overset { KCN }{ \longrightarrow } \underset { (B) }{ { C }_{ 6 }{ H }_{ 5 }-\underset { \overset { | }{ HO } }{ CH } -\underset { \overset { || }{ O } }{ C } -{ C }_{ 6 }{ H }_{ 5 } } \)
(iii) Benzaldehyde on treatment with sodium acetate and acetic anhydride form an acid, cinnamic acid it is (C).
\(\underset { (A) }{ { C }_{ 6 }{ H }_{ 5 }CHO } +\left( { CH }_{ 3 }{ CO } \right) O\overset { { CH }_{ 3 }COONa }{ \longrightarrow } \underset { (C) }{ { C }_{ 6 }{ H }_{ 5 }CH } =CH-COOH+CH_{ 3 }COOH\)
| Compound | Compound Name | Formula |
| A | Benzaldehyde | C6HsCHO |
| B | Benzoin | C6H5-CH-OHCO-C6H5 |
| C | Cinnamic acid | C6HsCH=CHCOOH |
13.
Acidic nature of acids:
(i) Acid molecule ionises to produce H+ ions in solution.
(ii) The carboxylate anion is stabilised by resonance.
Hence the cleavage of -COOH bond to release H+ is favoured, thereby making it to behave as acids.
(iii) Any factor that weakens the -COOH bond will facilitate the cleavage to release H+ more easily. The degree of ionisation is increased and acid becomes relatively a stronger acid.
(iv) When the following acids are compared
Their strength varies as the above order.
(v) Methyl group is a + I group (electron pair repelling group). Acid strength decreases: with increasing number of electron repelling substituent attached to the α- carbon atom.
The +1 effect is felt in increasing the strength of the -OH bond and the cleavage to form H+ becomes difficult. Hence they are weaker acid than formic acid (HCOOH) which does not have + I methyl group.
(vi) Acid strength increases with increase in electronegativity of substituents
This effect weakness the -O- H bond there by facilitating the removal of H+ from -OH group. This acid becomes stronger than formic acid.
14.
15.
Primary alcohols and aldehydes can easily be oxidised to the corresponding carboxylic acids with oxidising agents such as potassium permanganate (in acidic or alkaline medium), potassium dichromate (in acidic medium)
Example:
\(\underset{Ethyl \ alcohol}{ { CH }_{ 3 }{ CH }_{ 2 }OH}\overset { { H }^{ + }/{ K }_{ 2 }{ Cr }_{ 2 }{ O }_{ 7 } }{ \underset { (O) }{ \longrightarrow } } \underset{Acetaldehyde}{{ CH }_{ 3 }CHO}\underset { (O) }{ \longrightarrow }
\underset{Acetic \ acid}{{ CH }_{ 3 }COOH}\)
16.
(i) Cannizzaro reaction is a redox reaction which takes place only in aldehydes which do not have α- hydrogen atom.
(ii) Formaldehyde (HCHO) and benzaldehyde (C6H5CHO) do not have a-hydrogen atom and so they undergo Cannizzaro reaction.
(iii) But acetaldehyde CH3CHO contains 3 α-H atoms and it does not undergo Cannizzaro reaction.
17.
Ozone forms addition product with olefin called I ozonide, which on reductive cleavage gives aldehyde.
18.
2- Pentanone.
19.
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