1) draw a structure consistent with the following data: the ms shows a molecular ion at 59 amu. the...
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![Page 1: 1) Draw a structure consistent with the following data: The MS shows a molecular ion at 59 amu. The IR spectrum shows a double-humped strong absorbance](https://reader035.vdocuments.mx/reader035/viewer/2022062718/56649eba5503460f94bc2305/html5/thumbnails/1.jpg)
1) Draw a structure consistent with the following data: •The MS shows a molecular ion at 59 amu. •The IR spectrum shows a double-humped strong absorbance at around 3300 cm–1 (the only absorbance in the functional group region).
NH2
Odd molecular ion peak tells you there is a nitrogen.59-14=45 45/12=3 carbons 45-36=9 hydrogensC3H9N. 2(3)+2-9+1=0
The peak at 3300 cm–1 tells us that the N is part of an amine
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2) Either 2-butanone, 2-methyl-2-nitropropane, 3-pentanone, 1-nitropropane, nitroethane, or 2-bromopropane is responsible for the 1H NMR spectrum shown. Draw the structure of the responsible compound. (doublet and heptet)
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There are two signals in the spectra so we can eliminate 2-butanone, 2-methyl-2-nitropropane and 1-nitropropane because they have either more or less than 2 types of protons.
Next you can eliminate 3-pentanone because it would have a triplet and a quartet which is not seen in the spectra.
Also nitroethane can be eliminated because it would have a doublet and a quartet.
While the answer is 2-bromopropane which has a doublet and a heptet.
Br
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3) Either 2-butanone, 2-methyl-2-nitropropane, 3-pentanone, 1-nitropropane, nitroethane, or 2-bromopropane is responsible for the 1H NMR spectrum shown. Draw the structure of the responsible compound. (quartet, singlet and a triplet)
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Because there are 3 signals it is either 2-butanone or 1-nitropropane.
1-nitropropane should have a doublet, a quartet and a triplet
While our answer, 2-butanone should have a singlet, a quartet and a triplet..
O
O2N
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4) The molecular formula of a compound is C6H12O. Determine the
structure of the compound based on its molecular formula and its 13C NMR spectrum. (4 PEAKS)
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First 2(6)+2-12=2/2=1 so either a ring or double bond.
No peak shows up in the double bond region, C=C or C=O.
So that leaves a ring.
Four peaks and with this structure we have 4 different types of carbon.
OH
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5) Identify the compound with molecular formula C3H5Cl3 that
gives the following 13C NMR spectrum. (The resonance at 0 ppm is due to the TMS standard, not the unknown.)
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First, 2(3)+2-5-3=0 so no double bonds or rings.
Secondly there are 3 peaks, so 3 different kinds fo carbon.
So that leaves two choices that are correct.
Cl
Cl
Cl
Cl
Cl Cl
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6) What would the proton NMR peak look like for the indicated hydrogen?
CH
CH3
CH3O
H3C
Because the two sets of adjacent protons are equivalent this peak would follow the n+1 rule and be a septet.
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7) What type of electromagnetic radiation is used in nuclear magnetic resonance?
Radio waves
8) What is the most abundant peak in a mass spectrum called?
Base peak
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9) Using the MS and IR spectra attached (1A and 1B) propose the formula and structure of this compound. (106 and 108)
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MS shows a molecular ion peak at 106 and a M+2 peak at 108..
So 106-35=71 so 71/12=5 carbons so 71-60=11 hydrogens so
C5H11Cl 2(5)+2-11-1=0
However, there is a carbonyl peak in the IR
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So need to add an oxygen.
-CH4 gives C4H7ClO so 2(4)+2-7-1=2/2=1
So this is taken by the C=O bond.
One more thing, there is no peak at 2750 so no aldehyde, our carbonyl is a ketone
O
Cl
O
Cl
O Cl
The first one can be eliminated because of the base peak at 43 in the MS, a loss of 63 accounts for the loss of a –C2H4Cl group.
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10) What is the major product of the following reaction?
HBr
peroxide
Br
H
Br
BrBr
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11) What is the major product of the following reaction?
Br2
CCl4
Br BrBr
Br
Br
Br
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12) What is the major product of the following reaction?
HBr
H BrH
Br
Br
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8) What alkene should be used to synthesize the following alkyl bromide?
H Br
+Br
Br
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H Br
Br
Br
9) What alkene, when allowed to react with HBr, would produce the following alkyl bromide? (There is more than one correct answer.)
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10) What five-carbon alkene will give the same, single product whether it reacts with HBr in the presence or the absence of a peroxide?
H BrBr
Br
Br BrH BrBr
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11) Draw the major product of the following reaction, including its stereochemistry. (Use squiggly bonds to indicate a reaction that is not stereoselective.) Assume only one equivalent of the reagent is available to react with the substrate.
HBr
HBr
Br
Br
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12) Draw the major product of the following reaction, including its stereochemistry. (Use squiggly bonds to indicate a reaction that is not stereoselective.) Assume only one equivalent of the reagent is available to react with the substrate.
HBr
H BrBr
Br
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13)
Br Br
H Br
Br
+ Br
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14)
Br
H
Br
Br
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15)
NBS
hv
HBr
Br Br
Br
+ Br