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Question

Chemistry Question on Organic Reactions

Acid D formed in above reaction is :

A

Gluconic acid

B

Succinic acid

C

Oxalic acid

D

Malonic acid

Answer

Succinic acid

Explanation

Solution

Step-by-step Reaction Analysis:
1.Reaction of C2_2H5_5Br with alcoholic KOH:
C2_2H5_5Br (ethyl bromide) undergoes dehydrohalogenation with alcoholic KOH to form ethene (CH2_2 = CH2_2).
This step is represented as:
C2H5Bralc. KOHCH2=CH2  (A)\text{C}_2\text{H}_5\text{Br} \xrightarrow{\text{alc. KOH}} \text{CH}_2 = \text{CH}_2 \; (\text{A})
2. Addition of Br2_2 in CCl4_4:
Ethene reacts with bromine (Br2_2) in the presence of carbon tetrachloride (CCl4_4) to form 1,2-dibromoethane (BrCH2_2CH2_2Br).
This step is represented as:
CH2=CH2Br2/CCl4BrCH2CH2Br  (B)\text{CH}_2 = \text{CH}_2 \xrightarrow{\text{Br}_2/\text{CCl}_4} \text{BrCH}_2\text{CH}_2\text{Br} \; (\text{B})
3. Reaction of 1,2-dibromoethane with excess KCN:
The compound BrCH2_2CH2_2Br reacts with excess potassium cyanide (KCN) to form 1,2-dicyanoethane (NCCH2_2CH2_2CN).
This step is represented as:
BrCH2CH2BrExcess KCNNCCH2CH2CN  (C)\text{BrCH}_2\text{CH}_2\text{Br} \xrightarrow{\text{Excess KCN}} \text{NCCH}_2\text{CH}_2\text{CN} \; (\text{C})
4. Hydrolysis of 1,2-dicyanoethane:
Hydrolysis of 1,2-dicyanoethane (NCCH2_2CH2_2CN) in the presence of excess H3_3O+^+ (acidic medium) yields succinic acid (HOOCCH2_2CH2_2COOH).
This step is represented as:
NCCH2CH2CNH3O+ (Excess)HOOCCH2CH2COOH  (D)\text{NCCH}_2\text{CH}_2\text{CN} \xrightarrow{\text{H}_3\text{O}^+\text{ (Excess)}} \text{HOOCCH}_2\text{CH}_2\text{COOH} \; (\text{D})
Conclusion: The acid D formed is succinic acid.