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Student exercise 1

Student exercise 1. 2011/10/04 20111067 Hakuba Kitagawa. 1.1 the exact mass. Formula: C 7 H 16 S. Formula: C 13 H 20 O. (j). (k). MW = 12.00000 x 7 + 1.00783 x 16 + 31.9721 x 1 = 132.097 38 = 132.097. MW = 12.00000 x 13 + 1.00783 x 20 + 15.9949 x 1

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Student exercise 1

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  1. Student exercise 1 2011/10/04 20111067 Hakuba Kitagawa

  2. 1.1 the exact mass Formula: C7H16S Formula: C13H20O (j) (k) MW = 12.00000 x 7 + 1.00783 x 16 + 31.9721 x 1 = 132.09738 = 132.097 MW = 12.00000 x 13 + 1.00783 x 20 + 15.9949 x 1 = 192.1515 = 192.152

  3. 1.2 hydrogen deficiency Index = NC – NH/2 – NX/2 + NN/2 + 1 Formula: C7H16S Formula: C13H20O (j) (k) Index = 7 – 16/2 – 0/2 + 0/2 +1 = 0 Index = 13 – 20/2 – 0/2 + 0/2 +1 = 4 (3 double bonds + 1 ring)

  4. 1.3 molecular ion Most possible molecular ions are: : . + : . + or . + (j) (k)

  5. 1.4, 1.5 major fragmentation path way & mechanism Rule8. Hetero atom’s non-bonding electrons provide the cation charge with resonance stabilization (j-1) . - CH3CH2CH2 (j-2) . - CH3CH2

  6. 1.4, 1.5 major fragmentation path way & mechanism Rule3. the more substituted, the more likely is cleavage. (j-3) . - CH3CH2

  7. 1.4, 1.5 major fragmentation path way & mechanism Rule8. Hetero atom’s non-bonding electrons provide the cation charge with resonance stabilization (k-1) . - C6H4(CH2)5CH3

  8. 1.4, 1.5 major fragmentation path way & mechanism Rule8. Hetero atom’s non-bonding electrons provide the cation charge with resonance stabilization (k-2) . - CH2OH

  9. 1.4, 1.5 major fragmentation path way & mechanism Rule8. Hetero atom’s non-bonding electrons provide the cation charge with resonance stabilization (k-2) + + ・ - ・ (CH2)5CH3 + ・ ・ + - ・ C6H4 + +

  10. 1.4, 1.5 major fragmentation path way & mechanism Rule7. b-bond cleavage gives the resonance-stabilized benzyl ion or the tropylium ion (k-3) . - OH

  11. 1.4, 1.5 major fragmentation path way & mechanism Rule7. b-bond cleavage gives the resonance-stabilized benzyl ion or the tropylium ion (k-3) + + + (H- migration) +

  12. 1.4, 1.5 major fragmentation path way & mechanism Rearrangement (k-4) - H2O

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