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Question about Conceptual Organic chemistry

Discuss what you would observe after elution and visualization of a TLC plate having made the following mistakes in carrying out the analysis.

a. The solvent level in the developing jar was higher than the original line on which the samples were spotted.

b. Too much sample was applied to the TLC plate.

1) Suggest a suitable mechanism for the reaction of 9-fIuorenone with 2,4- dinitrophenylhydrazine to form the corresponding 2 ,4-d initrophenylhyd razone.

2) There are actually two isomeric 2,4-dinitrophenylhydrazones of 2- pentanone. Draw the structures of these isomers.

3) When 1-octene is treated with NBS, three monobromo straight-chain alkenes having molecular formula C9H17Br are Isolated from the reaction mixture. Identify these compounds and give each a suitable name.

4) Benzyl bromide (C6HsCH2Br) can be prepared by treating toluene with NBS in the presence of a peroxide initiator. Suggest a suitable mechanism to account for this reaction.

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