ISSUE:

Help with this please:
A compound A (C4 H9 Br) reacts with KOH to give a mixture of two compounds: B (C4 H8) and C (C4 H10 O).
Reaction of B with
HBr produces D an isomer of A. C reacts with K2 Cr2 O7 to give E (C4 H8 O) which, on reaction with toluene in the presence of AlCl3, gives two H,I of formula (C11 H14 O).
Write the structures of all the compounds from A to I. In which of them are there chiral carbons? Also mention what type of reaction is used in each stage of your reasoning.

help with this more please!!! although only a guide on how to do :'(

Hello, does the molecule E have only one oxygen?

A: 1-Bromobutane
B: 1-Butene comes from an elimination reaction (E-2)
C: 1-Butanol comes from a substitution reaction (SN-2)
D: 2-Bromobutane comes from an electrophilic addition reaction that follows Markovnikov's rule
E: Butanal comes from an oxidation reaction using Jones' reagent, always in the absence of water because otherwise it would easily form the carboxylic acid
H/I: The ortho and para isomers are obtained from the corresponding acylation de friedel crafts between toluene and butanal since the methyl group yields charge density due to an inductive effect to the ring, causing the formation of the meta isomer to not exist. With all this, it is evident that only
compound D will have a chiral carbon

Thank you for helping to solve the problem. PCC is normally used in DCM to stop oxidation to aldehyde, which made me wonder if product E was aldehyde or acid. Although it is true that the subsequent reaction of benzene with an acid would be extremely difficult.