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Organic Compounds

Hey !

Really stuck on this question can anyone help me ?

Predict the organic products for the following reactions:-

A)Propene and Br
B) But-1-ene and HCI
C) Butan-2-ol and Acidified Potassium and Dichromate (VI)
D) Propanol and Acidified Potassium Dichromate (VI)
E) Propanal and Tollens reagent (silver mirror)

Reply 1

Nitrogen

A. 2-bromopropane
b. 2-chlorobutane
C. Butanone
D. Propanoic acid if reflux, propanal if distillation

E. Propanoic acid.

Original post by Nitrogen

A. 2-bromopropane Are you sure? if he reacts Br₂ with propene then surely 1,2-dibromopropane is formed?
b. 2-chlorobutane Considering it is a double bond once again, wouldn't it be a mixture of 1-chlorobutane and 2-chlorobutane?
C. Butanone
D. Propanoic acid if reflux, propanal if distillation

Reply 4

Nitrogen

Original post by Oslo

My bad youre correct about A. For B the majority of the product you'd get would be 2-chlorobutane because its more stable than 1-chlorobutane.

Reply 5

Oslo

Original post by Nitrogen

My bad youre correct about A. For B the majority of the product you'd get would be 2-chlorobutane because its more stable than 1-chlorobutane.

I didn't realise that was the case; that's pretty cool, I guess different chemistry syllabuses vary in the theory they teach.

Reply 6

charco

Study Forum Helper

Original post by Nitrogen

My bad youre correct about A. For B the majority of the product you'd get would be 2-chlorobutane because its more stable than 1-chlorobutane.

It's not so much that the secondary isomer is more stable, it's that the secondary carbonium ion formed as an intermediate in the mechanism is more stable. This leads to 2-chlorobutane being the major product. It is called Markovnikov addition.

Reply 7

AtomicMan

Original post by KKP109

Which Propanol?

If propan-1-ol; Propanoic acid if refluxed to complete oxidation, Propanal if distilled to partial oxidation.
If propan-2-ol; Propanone.

Reply 8

KKP109

Thank you so much for your help