wiz-icon
MyQuestionIcon
MyQuestionIcon
1
You visited us 1 times! Enjoying our articles? Unlock Full Access!
Question

When CH3CH2Br is treated with aqueous NaCN, CH3CH2CN is formed while CH3CH2NC is formed when AgCN is used in the similar reaction. It is due to

A
Ionic nature of CN bond in NaCN
Right on! Give the BNAT exam to get a 100% scholarship for BYJUS courses
B
Covalent nature of AgC bond in AgCN
Right on! Give the BNAT exam to get a 100% scholarship for BYJUS courses
C
Covalent nature of CN bond in NaCN
No worries! We‘ve got your back. Try BYJU‘S free classes today!
D
Ionic nature of AgC bond in AgCN
No worries! We‘ve got your back. Try BYJU‘S free classes today!
Open in App
Solution

The correct option is B Covalent nature of AgC bond in AgCN
CN is the ambident nucleophile and can form different product with same substrate.
CH3CH2Br+NaCNCH3CH2CN+ CH3CH2+NC+NaBr Ethyl cyanide Ethyl isocyanide Major Minor
Here, NaCN is predominantly ionic and exist as free ions in solution. C site is more nucleophilic than N site and available to attack the ethyl bromide​. Hence, the major product will be ethyl cyanide​.
AgCN is predominantly covalent. Although C site is more nucleophilic than N site but not available in case of AgCN. Hence, lone pair of N attacks the ethyl chloride and isocyanide is formed as the major product.​ Hence, the major product will be ethylisocyanide.
CH3CH2Br+AgCNCH3CH2CN+CH3CH2NC+AgBr Ethyl cyanide Ethyl isocyanide Minor Major

flag
Suggest Corrections
thumbs-up
2
Join BYJU'S Learning Program
similar_icon
Related Videos
thumbnail
lock
Chemical Properties of Alcohols 2
CHEMISTRY
Watch in App
Join BYJU'S Learning Program
CrossIcon