A-2 cyclopropane cyclobutane cyclopentane cyclohexane cycloheptane cyclooctane methylc

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1 ethene H 2 H propene H 2 HH butene H 2 HH 2 H pentene H 2 H(H 2 ) 2 H hexene H 2 H(H 2 ) 3 H heptene H 2 H(H 2 ) 4 H octene H 2 H(H 2 ) 5 H nonene H 2 H(H 2 ) 6 H decene H 2 H(H 2 ) 7 H cis 2 cis-2-butene cis-h 3 H HH trans 2 trans-2-butene trans-h 3 H HH methylpropene H 2 (H 3 ) cis 2cis-2-pentene cis-h 3 H HH 2 H trans 2trans-2-pentene trans-h 3 H HH 2 H cyclohexene ethyne H H propyne H H butyne H H 2 H butyne H 3 H pentyne H (H 2 ) 2 H pentyne H 3 H 2 H methyl-1-butyne H H(H 3 ) hexyne H (H 2 ) 3 H hexyne H 3 (H 2 ) 2 H hexyne H 3 H 2 H 2 H heptyne H (H 2 ) 4 H octyne H (H 2 ) 5 H nonyne H (H 2 ) 6 H decyne H (H 2 ) 7 H A-1

2 A-2 cyclopropane cyclobutane cyclopentane cyclohexane cycloheptane cyclooctane methylcyclopentane methylcyclohexane cis 1,2 cis-1,2-dimethylcyclopentane trans 1,2 trans-1,2-dimethylcyclopentane dimethyl ether H 3 H diethyl ether H 3 H 2 H 2 H dipropyl ether H 3 (H 2 ) 2 (H 2 ) 2 H diisopropyl ether (H 3 ) 2 HH(H 3 ) dibutyl ether H 3 (H 2 ) 3 (H 2 ) 3 H divinyl ether H 2 HH H 2 35 diallyl ether H 2 HH 2 H 2 H H tetrahydrofuran dioxane

3 A-3 methanol H 3 H ethanol H 3 H 2 H propanol H 3 (H 2 ) 2 H butanol H 3 (H 2 ) 3 H pentanol H 3 (H 2 ) 4 H hexanol H 3 (H 2 ) 5 H heptanol H 3 (H 2 ) 6 H octanol H 3 (H 2 ) 7 H propanol H 3 HHH butanol H 3 HHH 2 H methyl-1-propanol (H 3 ) 2 HH 2 H methyl-2-propanol (H 3 ) 3 H mehyl-1-butanol (H 3 ) 2 H(H 2 ) 2 H methyl-2-butanol (H 3 ) 2 HH 2 H ,21 2,2-dimethyl-1-propanol (H 3 ) 3 H 2 H allyl alcohol H 2 HH 2 H cyclopentanol 5 H 9 H cyclohexanol 6 H 11 H benzyl alcohol 6 H 5 H 2 H methyl ethyl propyl isopropyl butyl isobutyl sec sec-butyl tert tert-butyl dec. pentyl hexyl dec. decomposition

4 A-4 methylamine H 3 NH ethylamine H 3 H 2 NH propylamine H 3 (H 2 ) 2 NH isopropylamine (H 3 ) 2 HNH butylamine H 3 (H 2 ) 3 NH isobutylamine (H 3 ) 2 HH 2 NH sec sec-butylamine H 3 H 2 H(H 3 )NH tert tert-butylamine (H 3 ) 3 NH cyclohexylamine 6 H 11 NH dimethylamine (H 3 ) 2 NH diethylamine (H 3 H 2 ) 2 NH dipropylamine (H 3 H 2 H 2 ) 2 NH dibutylamine (H 3 H 2 H 2 H 2 ) 2 NH trimethylamine (H 3 ) 3 N triethylamine (H 3 H 2 ) 3 N tripropylamine (H 3 H 2 H 2 ) 3 N aniline 6 H 5 NH benzene 6 H benzaldehyde 6 H 5 H benzamide 6 H 5 NH benzoic acid 6 H 5 H bromobenzene 6 H 5 Br chlorobenzene 6 H 5 l nitrobenzene 6 H 5 N phenol 6 H 5 H styrene 6 H 5 H H toluene 6 H 5 H

5 A-5 formic acid HH acetic acid H 3 H propionic acid H 3 H 2 H butanoic acid H 3 (H 2 ) 2 H pentanoic acid H 3 (H 2 ) 3 H hexanoic acid H 3 (H 2 ) 4 H heptanoic acid H 3 (H 2 ) 5 H octanoic acid H 3 (H 2 ) 6 H nonanoic acid H 3 (H 2 ) 7 H decanoic acid H 3 (H 2 ) 8 H oxalic acid HH 189 malonic acid HH 2 H 136 succinic acid H(H 2 ) 2 H 185 glutaric acid H(H 2 ) 3 H 98 adipic acid H(H 2 ) 4 H 151 pimelic acid H(H 2 ) 5 H 106 phthalic acid 1,2-6 H 4 (H) maleic acid cis-hh HH fumaric acid trans-hh HH 302 acetyl chloride H 3 l propionyl chloride H 3 H 2 l butyryl chloride H 3 (H 2 ) 2 l valeryl chloride H 3 (H 2 ) 3 l acetic anhydride H 3 ()()H succinic anhydride

6 A-6 methyl formate HH ethyl formate HH 2 H methyl acetate H 3 H ethyl acetate H 3 H 2 H propyl acetate H 3 (H 2 ) 2 H methyl propionate H 3 H 2 H ethyl propionate H 3 H 2 H 2 H methyl butyrate H 3 H 2 H 2 H ethyl butyrate H 3 H 2 H 2 H 2 H formamide HNH d acetamide H 3 NH propanamide H 3 H 2 NH butanamide H 3 (H 2 ) 2 NH pentanamide H 3 (H 2 ) 3 NH d formaldehyde HH acetaldehyde H 3 H propionaldehyde H 3 H 2 H butylaldehyde H 3 (H 2 ) 2 H pentanal H 3 (H 2 ) 3 H hexanal H 3 (H 2 ) 4 H heptanal H 3 (H 2 ) 5 H octanal H 3 (H 2 ) 6 H 171 nonanal H 3 (H 2 ) 7 H 192 decanal H 3 (H 2 ) 8 H benzaldehyde 6 H 5 H

7 A-7 acetone H 3 H butanone H 3 H 2 H pentanone H 3 (H 2 ) 2 H hexanone H 3 (H 2 ) 3 H heptanone H 3 (H 2 ) 4 H octanone H 3 (H 2 ) 5 H nonanone H 3 (H 2 ) 6 H decanone H 3 (H 2 ) 7 H pentanone H 3 H 2 H 2 H hexanone H 3 H 2 (H 2 ) 2 H heptanone H 3 H 2 (H 2 ) 3 H acetophenone H 3 6 H propiophenone H 3 H 2 6 H

8 = H 3 = H 2 = H (ppm) H 2 H H F l Br I H H H 2 N N H 2 N 2 N + 3 N N NH 2 N A-8

9 A cm H 3 H 3 ( ) H 2 H 2 H 2 H 2 ( ), H 2 ( N) H n H H 2v 2 H H H H H 2v 2 H H H 2 H 2 H 2 (m-high) H 2 H 2 H H 3 H H (m-high) H ( ) 4000 cm μm

10 A cm H H 2 H 2 H 2 H H H H 2 H H H 2 H 2 NH 2 NH N 2 NH 2 H 2 H 2 H NH 2 NH 2 H 2 NH H 2 H NH H NH (H 2 ) 3 N N 2 NH 3 l 2v NH N N N + i, P, H H H 2 H 2 PH P P ih i H 3 i 4000 cm μm

11 A-11 2 F 2 F 3 F F Br 2 Br 3 Br l 2 l 3 l NH 4 + ( 3 ) 2 ( HN ( (N 3 ) ) 2 ) 2 N 2 N 2 N N ( 4 ) H NH 2 2 (P 4 ) 3 () 3 P H 2 P P H NH H N N NH H H H NH.μ

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