I have an organic

Question

I have an organic

chemistry question, I need help with all parts (photos attached). Thanks a ton muiplicity is tough to grasp.

3.
(20 marks) When 2,2-dimethyl-4-bromopentane is treated with silver(I) in the presence of water,
the reaction can give a variety of products: direct substitution or formation of an alcohol via
carbocation rearrangement(s), or elimination to form an alkene:
Alcohols
Ag*, H20
(substitution)
-Br
Intermediate
Rearrangement(s)
Alkenes
elimination)
The following 1H and 13C NMR spectra were taken of one product A obtained from this reaction.
Complete spectra are provided: 1H NMR from 0.5 to 5.0 ppm and 13C NMR from 0 to 160 ppm. No other
peaks are present in these spectra.
1H NMR
3H, doublet
3H, singlet
3H, triplet
2 overlapping
peaks
13(
2H, singlet
2H, muiplet
1H, sextet
160 140 120 160 80
ppm
80 60
(a) Deduce a molecular formula for this compound.
(b) Is the product a substitution or elimination product?
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