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ORGANIC CHEMISTRY –II
3. CARBONYL COMPOUNDS
PREVIOUS EAMCET BITS
1. What are the X and Y in the following reaction sequence : C2 H 5OH ⎯⎯
Cl2
→ X ⎯⎯
Cl2
→Y
(2009 E)
1) C2 H 5OH , CH 3CHO 2) CH 3CHO, CH 3CO2 H
3) CH 3CHO, CCl3CHO 4) C2 H 5Cl , CCl3CHO

Ans : 3
Sol: Reaction CH 3 .CH 2OH + Cl2 → CH 3CHO + 2 HCl
X
CH 3CHO + 3Cl2 → CCl3 .CHO + 3HCl
Y

2. The synthesis of crotonaldehyde from acetaldehyde is an example of ………… reaction

(2009 E)
1) Nucleophilic addition 2) Elimination
3) Electrophilic addition 4) Nucleophilic addition - elimination
Ans : 4
Sol: Reactions:
OH − or H +
2CH 3CHO ⎯⎯⎯⎯ → CH 3 − CH ( OH ) CH 2CHO
Aldol
Δ
CH 3 − CH − CH 2 CHO ⎯⎯ → CH 2 − CH = CH − CHO + H 2 O
|
OH
Crotonaldehyde
3. In which of the following reations, the final product is 2-methyl1-2-propanol ?
(2009 M)
( i ) CH 3 MgBr / dry ether
1) CH 3CHO ⎯⎯⎯⎯⎯⎯⎯ ( ii ) H O +
→
2

( i ) C2 H 5 MgBr / dry ether

2) CH 3CHO ⎯⎯⎯⎯⎯⎯⎯ ( ii ) H 3O +
→
( i ) CH 3 MgBr / dry ether
3) CH 3COCH 3 ⎯⎯⎯⎯⎯⎯⎯ ( ii ) H 3O +
→
( i ) CH 3 MgBr / wet ether
4) CH 3COCH 3 ⎯⎯⎯⎯⎯⎯⎯ ( ii ) H 3O +
→
Ans : 3
H 3C H 3C OMgBr H 3C OH
+
C == O + CH 3 MgBr → C ⎯⎯⎯
H3 O
→ C
Sol:
H 3C H 3C CH 3 H 3C CH 3

2 – methyl-2-propanol

4. In which of the following reaction, chlorine acts as an oxidizing agent ? (2008 E)

(i) CH 3CH 2OH + Cl2 → CH 3CHO + HCl
(ii) CH 3CHO + Cl2 → CCl3 .CHO + HCl
(iii) CH 4 + Cl2 ⎯⎯
hv
→ CH 3Cl + HCl
1) (i) only 2) (ii) only 3) (i) and (iii) 4) (i), (ii) and (iii)
Ans : 4
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−2 +1 +2 +1 −2
Sol: C H O ⎯⎯⎯
2 6→C H O Oxdn 0
2 4 2

C2−1 H 4+1O −2 ⎯⎯⎯

Oxdn
→ C2+2Cl3−1 H +1O −2
C −4 H 4+1 ⎯⎯⎯
Oxdn
→ C +2 H 3+1Cl −1

5. The compound that reacts with CH3 MgBr to yield methane as one of the products is
(2008 M)
1) CH 3CHO 2) CH 3COCH 3 3) CH 3COOCH 3 4) CH 3CH 2OH
Ans : 4
Sol: C2 H 5OH + CH 3 MgBr → CH 4 + Mg ( OC2 H 5 ) I

6. Which one of the following reactions is called Rosenmund reaction ? (2007 M)

1) Aldehydes are reduced to alcohols 2) Acids are converted to acid chlorides
3) Alcohols are reduced to hydrocarbons
4) Acid chlorides are reduced to aldehydes
Ans : 4
Sol: Rosenmund’s reaction :
CH 3COCl + H 2 ⎯⎯⎯⎯
Pd / BaSO4
→ CH 3CHO + HCl

7. Which of the products is formed when acetone is reacted with barium hydroxide solution ?
(2006 E)
O CH 3 O
|| | ||
1) CH 3 − C − CH 2 − C − CH 3 2) CH 3 − C − CH − CH − CH 3
| | |
OH CH 3 CH 3
O OH OH
|| | |
3) CH 3 − C − CH − CH − CH 3 4) CH 3 − C − C − CH 3
| | | |
OH CH 3 CH 3 OH
Ans : 1
Sol: Reaction
Ba ( OH )
⎯⎯⎯⎯
2CH 3 .CO.CH 3 ←⎯⎯⎯
2
⎯→
OH
|
CH 3 − C − CH 2 .CO.CH 3
|
OH

8. When acetaldehyde is heated with Fehling solution, a red precipitate is formed. Which of the
following is that
(2006 E)
1)Cu2O 2) Cu 3) CuO 4) CuSO4
Ans : 1
Sol: Reaction
CH 3CHO + 2Cu 2 + 5OH − → CH 3COO − + Cu2O ↓ +3H 2O

9. Which of the following compounds can give iodoform test ? (2006 M)

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1) Formaldehyde 2) Acetaldehyde 3) Diethyl ketone 4) Diethyl ether
Ans : 2
Sol: Reaction
CH 2CHO + 3I 2 + 4 NaOH → H COONa + CHI 3 + 3H 2O + 3 NaI

10. What reagent is used in the Rosenmund reduction ? (2006 M)

1) H 2 | Pd − BaSO4 2) LiAIH4
CH 2 − OH
3) NH 2 NH 2 | KOH | | 4) Zn – Hg |HCl
CH 2 − OH
Ans : 1
Sol: Rosenmund reduction
Pd − BaSO4
CH 3COCl + H 2 ⎯⎯⎯⎯ → CH 3CHO + HCl

11. Which of the following compounds is the reactant in Rosenmund’s reaction? (2005 E)
1) CH3CO2H 2) CH2CHO 3) CH3CH2Cl 4) CH3COCl
Ans : 4
Sol: Rosenmund reduction
Pd − BaSO4
CH 3COCl + H 2 ⎯⎯⎯⎯ → CH 3CHO + HCl

12. In the reaction, C2 H 5OH ⎯⎯⎯ Cu

3000 C
→X ? (2005 E)
(Vapour)
The molecular formula of X is :
1) C2H6O 2) C4H10O 3) C2H4O 4) C2H6
Ans : 3
Sol: Reaction
C2 H 5OH ⎯⎯⎯⎯
Cu catalyst
3000 C
→ CH 3CHO + H 2

13. Identify X and Y in the following sequence of reactions (2005 M)

CH 3CHO ⎯⎯⎯ HNO3
→ X ⎯⎯⎯P4O10
→Y

X Y
1) C2 H 5OH C2 H 4
2) CH 3CO 2 H ( CH3CO )2 O
3) CH 3CO 2 H CH 3CO 2 CH 3
4) C2 H 5OH CH 3CO 2 H

Ans : 2
Sol: Reaction
CH 3CHO ⎯⎯⎯
HNO3
+( 0)
→ CH 3COOH
(X)
→ ( CH 3CO )2 O + H 2O
2CH 3COOH ⎯⎯⎯ P4O10
Δ

(Y)

14. A compound X undergoes reduction with LiAlH4 to yield Y. When vapours of Y are passed over
freshly reduced copper at 3000C, X is formed. What is Y ? (2005 M)
1) CH 3COCH 3 2) CH 3CHO 3) CH 3CH 2OH 4) CH 3 − O − CH 3
Ans : 3
Sol: Reaction
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CH 3CHO ⎯⎯⎯→ CH 3 .CH 2OH
LiAlH 4

(X) (Y)
CH 3 . CH 2OH ⎯⎯⎯Cu
3000 C
→ CH 3 . CHO + H 2
(Y) (X)

15. Identify ‘actaldoxime’ (2004 E)

1) CH 3CH = N − NH 2 2) CH 3CH = N − OH
3) ( CH 3 )2 C = N − OH 4) CH 2 = N − OH
Ans : 2
Sol: Acetaldoxime structure CH 2CH = N − OH

16. The product formed in the aldol condensation of acetaldehyde (2004 M)

1) CH 2CH 2CH ( OH ) CHO 2) CH 2CH ( OH ) CH 2CHO
3) CH 3CH ( OH ) COCH 3 4) CH 3CH 2CH 2CHO
Ans : 2
Sol: Aldol condensation of acetaldehyde reaction.
2CH 3CHO ⎯⎯⎯⎯OH − or H +
→ CH 3 − CH ( OH ) CH 2CHO

17. What is X in the following reaction 2CH 3COCH 3 ⎯⎯⎯⎯

Ba ( OH ) 2
→x (2002 E)
OH O OH
| || |
1) CH 3 − C − CH 2 − C − CH 3 2) CH 3 − C − CH 2 − CHO
| |
CH 3 CH 3
CH 3 − CH − CH − C − CH 3
3) CH 3CH ( CH 3 ) CH 2COCH 3 4) | | ||
CH 3 OH O
Ans : 1
OH O
| ||
Ba ( OH )2
Sol: 2CH 3 . CO.CH 3 ⎯⎯⎯⎯
→ CH 3 − C − CH 2 − C − CH 3
|
CH 3
Diacetone alcohol

18. Acetaldehyde is reduced with hydrogen in the presence of nickel. What is the compound formed
(2002 M)
1) Ethanol 2) n-propanol 3) Methanol 4) Isopropanol
Ans : 1
Sol: CH 3CHO + H 2 ⎯⎯
Ni
→ CH 3 .CH 2OH

19. Dry distillation of a mixture calcium acetate and calcium formate forms… (2001 E)
1) Methanol 2) Ethanal 3) Ethanol 4) Acetone
Ans : 2
Sol : Dry distillation of Calcium acetate and Calcium formate gives acetaldehyde.

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Ca ( CH 3COO )2 + Ca ( HCOO )2 ⎯⎯
Δ
→ 2CH 3CHO + 2CaCO3

20. In the following reaction C2 H 2 ⎯⎯⎯⎯⎯⎯→ H 2O ⎯⎯

→ CH 3CHO. What is X?
X ←⎯
⎯
HgSO / H SO ,600 C
4 2 4

(2001 M)
1) CH 3CH 2OH 2) CH 3 − O − CH 3 3) CH 3CH 2CHO 4) H 2C = CHOH
Ans :4
OH O
Sol : CH ≡ CH + H 2O ⎯⎯⎯→ HgSO4
| CH 3 − C
H 2 SO4 .60° C
CH 2 = CH ⎯⎯⎯⎯→ tautomerism
H
Acetylene Vinyl alcohol Acetaldehyde

In the above reaction, intermediate compounds is CH2 = CHOH

21. In chloroethane, the carbhon bearing halogen is bonded to … hydrogen (s). It is called … alkyl halide.
(2002 E)
1) two, primary 2) three, primary 3) two, secondary 4) one, tertiary
Ans: 1
H H
| |
Sol: H − C − C − Cl
| |
H H
C bounded to 2 H atoms ∴ it is primary alkyl halide.

22. Ethanal is reacted with acidified K2Cr2O7. What is the product formed ? (2001 M)
1) C2H5OH 2) CH3COOH 3) C2H6 4) CCl3CHO
Ans : 2
Sol: Acetaldehyde (Ethanal) undergoes oxidation to acetic acid when treated with acidified K 2Cr2O7 .
CH 3CHO + ( O ) ⎯⎯⎯⎯⎯
+
K 2Cr2O7 / H
→ CH 3COOH −

23. What is X in the following reaction ? 2CH 3CHO ⎯⎯⎯⎯

dil NaOH
→X (2000 E)
CH 3 − CH − CHO CH 3 − C − CH 2 − CHO
1) | 2) ||
O O

CH 3 − CH − CH 2 − CHO CH 3 − CH 2 − CH − CHO
3) | 4) |
OH OH
Ans : 3
OH
|
Sol: 2CH 3 − CHO ⎯⎯⎯⎯
dil NaOH
→ CH 3 − CH − CH 2 − CHO
(Aldol reaction)

24. Which of the following converts acetone to acetone oxime ? (2000 E)

1) H 2 N − NH 2 2) 2,4- DNP 3) C6 H 5 NHNH 2 4) NH 2OH
Ans : 4
Sol:
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CH 3 − C = O + H 2 N − OH ⎯⎯
→ CH 3 − C = N − OH + H 2 O
| |
CH 3 CH 3
Acetooxime

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