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**Don`t have to answer them all. Anyhelp appreciated! Draw the skeletal structur

ID: 685178 • Letter: #

Question

**Don`t have to answer them all. Anyhelp appreciated!

Draw the skeletal structure of the compound whose structure wouldbe consistent with the following information:

(a) molecular formula C4H10O whoseproton NMR spectrum contains a downfield quartet and an upfieldtriplet with relative integration 2:3




(b) molecular formula C5H12O whoseproton NMR spectrum contains a septet, quartet, triplet anddoublet.




(c) molecular formula C3H8O whoseproton NMR spectrum contains a singlet, triplet and quartet.



(d) molecular formula C6H14O whoseproton NMR spectrum contains a septet and doublet with relativeintegration 1:6.



**Don`t have to answer them all. Anyhelp appreciated!


Explanation / Answer

(won't let me insert diagrams) a) IHD = 1/2 [(2(4)+2)-(10)]=0 No bonds/rings (possiblefunctional groups include alcohol or ether) 2 signals = 2 sets of hydrogens (with four carbons, structure mustbe a symmetrical ether) 2:3 ratio, downfield quartet, upfield triplet = Structure mustcontain 2 methylene units and 2 methyl units Structure: Diethyl ether b) IHD = 0 No bonds/rings (possible functional groupsinclude alcohol or ether) 4 signals = 4 sets of hydrogens Structure: 2-ethoxypropane (Isopropyl Etyl ether) c) IHD = 0 No bonds/rings (possible functional groupsinclude alcohol or ether) 3 signals = 3 sets of hydrogen Structure: Methoxyethane (Methyl Ethyl Ether) d) IHD = 0 No bonds/rings (possible functional groupsinclude alcohol or ether) 2 signals = 2 sets of hydrogens 1:6 ratio = 2H in one signal (septet), 12H in the other(doublet) Molecule must be symmetrical Structure: Diisopropyl ether