ORGANIC CHEMISTRY Give structures for isomers of octane (C_8H_18) that will give

Question

ORGANIC CHEMISTRY

Give structures for isomers of octane (C_8H_18) that will give the following number of peaks in the given carbon NMR spectrum. An isomer that has 5 peaks in its normal (not DEPT)^13C NMR spectrum. An isomer that has exactly 4 peaks in its normal (not DEPT)^13C NMR spectrum An isomer that has exactly 3 "down" peaks in its DEPT 135^13C NMR spectrum. (Can have any number of "up" peaks.) An isomer that has exactly 2 peaks in its DEPT 90^13C NMR spectrum. An isomer that has exactly 3 peaks in its DEPT 90^13C NMR spectrum. An isomer that has exactly 2 peaks in its normal (not DEPT) 613C NMR spectrum

Explanation / Answer

1) An isomer that has exactly 5 peaks in normal 13C CH3-CH2-CH2-CH(CH3)CH2-CH2-CH3 4-methyl heptane There are 5 equivalent sets of carbon atom in the above structure. 2) Isomer with 4 peaks in normal 13C NMR CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH3 (n-octane) It has 4 sets of equivalent carbon atoms, therefore it show 4 peaks in 13C spectrum. 3) Isomer with 3 down peaks in DEPT 135 In DEPT 135, only CH2 carbon peaks are down, therefore the structure is (CH3)3C-CH2-CH2-CH2-CH3 2,2-Dimethyl hexane 4) Isomer with 2 peaks in DEPT 90 DEPT 90 show only CH peaks in the 13C spectrum. (CH3)2CH-CH2-CH2-CH(CH3)2 5)Isomer with 3 peaks in DEPT90 It should have 3 CH groups (CH3)2CH-CH(CH3)-CH(CH3)2 2,3,4-trimethyl pentane 6) Isomer with 2 peaks in normal 13C The structure must have two sets of equivalent carbon atoms. (CH3)3C-C(CH3)3 one peak for carbon of CH3 and other for carbon with no hydrogen.

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