ORGANIC CHEMISTRY –II

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

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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 →

3.

Aldol CH 3 − CH − CH 2 CHO ⎯⎯ CH 2 − CH = CH − CHO + H 2 O → | OH Crotonaldehyde 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 +
Δ
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 C == O + CH 3 MgBr → C H 3C H 3C OMgBr H 3C OH
H3 O ⎯⎯⎯ →
+

Sol:

C

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
hv (iii) CH 4 + Cl2 ⎯⎯ CH 3Cl + HCl → 1) (i) only 2) (ii) only

3) (i) and (iii)

4) (i), (ii) and (iii)

Ans : 4
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Sol:

C H O ⎯⎯⎯ C H O →
Oxdn 0 2

−2 2

+1 6

+2

+1 4

−2 2

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Organic Chemistry – II

Oxdn + C2−1 H 4 1O −2 ⎯⎯⎯ C2 2Cl3−1 H +1O −2 → +
+ Oxdn C −4 H 4 1 ⎯⎯⎯ 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) 2) CH 3COCH 3 3) CH 3COOCH 3 4) CH 3CH 2OH 1) CH 3CHO

Ans : 4 Sol: C2 H 5OH + CH 3 MgBr → CH 4 + Mg ( OC2 H 5 ) I
(2007 M) Which one of the following reactions is called Rosenmund reaction ? 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 : Pd / BaSO4 CH 3COCl + H 2 ⎯⎯⎯⎯ CH 3CHO + HCl →

6.

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
O || | | CH 3 CH 3 OH OH | | OH | CH 3
Ba ( OH )

| |

3) CH 3 − C − CH − CH − CH 3

4) CH 3 − C − C − CH 3
| CH 3 OH

Ans : 1 Sol: Reaction

2 ⎯⎯⎯⎯ → 2CH 3 .CO.CH 3 ←⎯⎯⎯ ⎯ 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 ? Powered by 2 myengg.com
(2006 M)

1) Formaldehyde

Powered by myengg.com 2) Acetaldehyde 3) Diethyl ketone

Organic Chemistry – II 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 ? 2) LiAIH4 1) H 2 | Pd − BaSO4 CH 2 − OH 3) NH 2 NH 2 | KOH | | CH 2 − OH Ans : 1 Sol: Rosenmund reduction Pd − BaSO4 CH 3COCl + H 2 ⎯⎯⎯⎯ CH 3CHO + HCl → Which of the following compounds is the reactant in Rosenmund’s reaction? (2005 E) 2) CH2CHO 3) CH3CH2Cl 4) CH3COCl 1) CH3CO2H Ans : 4 Sol: Rosenmund reduction Pd − BaSO4 CH 3COCl + H 2 ⎯⎯⎯⎯ CH 3CHO + HCl → 11. 12.
Cu In the reaction, C2 H 5OH ⎯⎯⎯ X ? → 3000 C (Vapour) The molecular formula of X is : 2) C4H10O 1) C2H6O

(2006 M)

4) Zn – Hg |HCl

(2005 E)

3) C2H4O

4) C2H6

Ans : 3 Sol: Reaction Cu catalyst C2 H 5OH ⎯⎯⎯⎯ CH 3CHO + H 2 → 3000 C 13. Identify X and Y in the following sequence of reactions HNO3 P4O10 CH 3CHO ⎯⎯⎯ X ⎯⎯⎯ Y → →
X C2 H 5OH Y C2 H 4 (2005 M)

1) 2) 3) 4)

CH 3CO 2 H CH 3CO 2 H C2 H 5OH

( CH3CO )2 O
CH 3CO 2 CH 3 CH 3CO 2 H

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

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

Ans : 3 Sol: Reaction
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Powered by myengg.com CH 3CHO ⎯⎯⎯ CH 3 .CH 2OH → (X) (Y) Cu CH 3 . CH 2OH ⎯⎯⎯ CH 3 . CHO + H 2 → 3000 C
LiAlH 4

Organic Chemistry – II

(Y) 15. Identify ‘actaldoxime’ 1) CH 3CH = N − NH 2

(X)
(2004 E) 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) 2) CH 2CH ( OH ) CH 2CHO 1) CH 2CH 2CH ( OH ) CHO 3) CH 3CH ( OH ) COCH 3 4) CH 3CH 2CH 2CHO

Ans : 2 Sol: Aldol condensation of acetaldehyde reaction. OH − or H + 2CH 3CHO ⎯⎯⎯⎯ CH 3 − CH ( OH ) CH 2CHO →
17.
Ba ( OH ) 2 → (2002 E) What is X in the following reaction 2CH 3COCH 3 ⎯⎯⎯⎯ x 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 Ans : 1
OH

4)

| | || CH 3 OH O

O

|

||

Sol:

2CH 3 . CO.CH 3 ⎯⎯⎯⎯ CH 3 − C − CH 2 − C − CH 3 →
|
CH 3 Diacetone alcohol

Ba ( OH )2

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 Ni CH 3CHO + H 2 ⎯⎯ CH 3 .CH 2OH → Sol: 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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19.

Powered by myengg.com Δ Ca ( CH 3COO )2 + Ca ( HCOO )2 ⎯⎯ 2CH 3CHO + 2CaCO3 →

Organic Chemistry – II

20.

H 2O ⎯⎯ → In the following reaction C2 H 2 ⎯⎯⎯⎯⎯⎯→ X ←⎯ CH 3CHO. What is X? ⎯ HgSO / H SO ,600 C
4 2 4

1) CH 3CH 2OH Ans :4 Sol :

2) CH 3 − O − CH 3 OH |

(2001 M) 3) CH 3CH 2CHO 4) H 2C = CHOH
O CH 3 − C
tautomerism

CH ≡ CH + H 2O ⎯⎯⎯ →
HgSO4 H 2 SO4 .60° C

CH 2 = CH ⎯⎯⎯⎯ →
Vinyl alcohol

H
Acetaldehyde

Acetylene

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. Ethanal is reacted with acidified K2Cr2O7. What is the product formed ? (2001 M) 2) CH3COOH 3) C2H6 4) CCl3CHO 1) C2H5OH

22.

Ans : 2 Sol: Acetaldehyde (Ethanal) undergoes oxidation to acetic acid when treated with acidified K 2Cr2O7 .
K 2Cr2O7 / H CH 3CHO + ( O ) ⎯⎯⎯⎯⎯ CH 3COOH − →
+

23.

dil NaOH → What is X in the following reaction ? 2CH 3CHO ⎯⎯⎯⎯ X CH 3 − CH − CHO CH 3 − C − CH 2 − CHO

(2000 E)

1)

| O

2)

|| O

CH 3 − CH − CH 2 − CHO

CH 3 − CH 2 − CH − CHO

3) Ans : 3 Sol:

| OH

4)

| OH

OH | dil NaOH 2CH 3 − CHO ⎯⎯⎯⎯ CH 3 − CH − CH 2 − CHO → (Aldol reaction)

24. Ans : 4 Sol:

Which of the following converts acetone to acetone oxime ? 2) 2,4- DNP 3) C6 H 5 NHNH 2 1) H 2 N − NH 2

(2000 E) 4) NH 2OH

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Powered by myengg.com → CH 3 − C = O + H 2 N − OH ⎯⎯ CH 3 − C = N − OH + H 2 O | | CH 3 CH 3
Acetooxime

Organic Chemistry – II

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