제1부 예비편 · ······························· 9

1 기본 유기화학 실험 ····························· 11

  1. 실험기구 · ································ 11

  2. 측정과 옮기기 ······························· 13

  3. 젓기와 섞기 ································ 14

  4. 가열과 냉각 ································ 15

2 실험실 안전 수칙 · ····························· 19

  1. 일반적인 수칙 ······························· 19

  2. 복장 ···································· 20

  3. 화재 예방 · ································ 20

  4. 독성 물질과 부식성 물질 · ························ 22

  5. 그 밖의 실험실 위험 요소들 ························ 23

  6. 폐기물 처리 ································ 26

  7. 응급 처치 · ································ 27

3 추출, 증류 및 재결정 ···························· 29

  1. 추출 ···································· 29

  2. 증류 ···································· 33

  3. 재결정 ·································· 41

4 크로마토그래피 · ······························ 45

  1. 얇은 막 크로마토그래피 ·························· 45

  2. 관 크로마토그래피 · ··························· 49

  3. 기체 크로마토그래피 · ·························· 52

  4. 고성능 액체 크로마토그래피 ······················· 60

  5. 광학 활성의 측정 · ···························· 63

5 구조 결정과 분광법 ····························· 65

  1. 전자기 복사선과 분광법의 원리 · ····················· 65

  2. 적외선 분광법 ······························· 67

  3. 핵자기공명 분광법 · ··························· 71

  4. 가리움과 화학적 이동 ··························· 72

  5. 1H NMR의 화학적 이동과 적분 ······················ 73

  6. 1H NMR의 스핀-스핀 갈라짐 ······················· 75

  7. 13C NMR 분광법 · ··························· 78

  8. DEPT 13C 스펙트럼 · ·························· 79

  9. 2차원 NMR 스펙트럼 ·························· 80

  10. 자외선 및 가시광선 분광법 ······················· 83

  11. 질량분석법 · ······························ 85

제2부 실험편 · ······························ 87

1 알켄과 알카인 · ······························· 89

  1. 알켄의 구조 ································ 89

  2. 반응성 ·································· 90

  3. 알켄의 제법 ································ 91

  실험 1.1 ▶ 3-Pentanol의 탈수 반응（알켄의 제조） · ··········· 93

  실험 1.2 ▶ trans-1,2-dibromocyclohexane의 합성 ········· 97

  4. 알카인의 구조 ······························ 101

  5. 알카인의 성질 ······························ 101

  6. 알카인의 제법 ······························ 102

2 할로알케인 · ································· 103

  1. 할로알케인의 제법 · ·························· 103

  2. 유기금속 화합물-Grignard 시약 ···················· 104

  실험 2.1 ▶ 1-Iodohexane의 합성 · ················· 105

  3. 친핵성 치환 반응 · ··························· 109

  4. SN2 반응 ································ 109

  5. SN2 반응에 영향을 미치는 인자 ···················· 110

  6. SN1 반응 ······························· 111

  실험 2.2 ▶ Silver nitrate 시험 · ··················· 112

  실험 2.3 ▶ n-Hexyl ethyl ether의 합성(Williamson synthesis) · · 115

  7. 할로알케인의 제거 반응 ························· 119

3 산화-환원 반응 ································ 121

  1. 산화 반응 · ······························· 121

  2. 환원 반응 · ······························· 124

  실험 3.1 ▶ 3-pentanone의 합성 ··················· 126

  실험 3.2 ▶ Cyclohexanone의 합성 ················· 129

  실험 3.3 ▶ Pyridine-2-carboxylic acid(picolinic acid)

  실험 3.3 ▶ hydrochloride의 합성 · ················· 133

  실험 3.4 ▶ p-toluidine의 합성 ···················· 137

  실험 3.5 ▶ 1-(3-nitrophenyl) ethanol의 합성 ············ 141

4 친전자성 방향족 치환 반응 · ······················· 143

  1. 벤젠의 구조와 결합 · ·························· 143

  2. 벤젠의 궤도함수 모형과 안정도 · ···················· 143

  3. 친전자성 치환 반응 · ·························· 144

  4. 할로젠화 반응 ······························ 145

  5. 치환된 벤젠의 상대적 반응성 · ····················· 148

  6. 치환된 벤젠의 위치 선택성 · ······················ 149

  7. 활성 효과와 배향기의 중요성 · ····················· 151

  8. 산화-환원 반응 · ···························· 151

  9. 방향족성에 대한 일반화 ························· 152

  10. 헤테로고리 방향족 화합물 ······················· 152

  실험 4.1 ▶ 1,2,4,5-Tetrabromobenzene의 합성: Bromination · 153

  실험 4.2 ▶ p-Nitrotoluene의 합성 · ················· 157

  실험 4.3 ▶ m-Dinitrobenzene의 합성 ················ 161

  11. 친핵성 방향족 치환 반응 ························ 165

  실험 4.4 ▶ n-(n-Butyl)-2,4-dinitroaniline의 합성 · ········ 166

5 알코올, 페놀 및 에터 ···························· 169

  1. 알코올의 수소결합 · ·························· 169

  2. 알코올과 페놀의 산성도와 염기성도 ··················· 170

  3. 알코올의 제법 ······························ 171

  4. 알코올의 탈수 반응 · ·························· 172

  5. 알코올의 할로젠화 반응 ························· 173

  6. 알코올의 산화 · ···························· 174

  7. 페놀의 반응 ······························· 174

  8. 에터의 합성: Williamson 에터 합성법 ················ 176

  9. 에터의 산 분해 반응 ··························· 176

  10. Oxacyclopropane의 고리열림 반응 ················ 177

  11. 알코올, 페놀 및 에터의 황 유사체 ··················· 178

  실험 5.1 ▶ 환원 반응을 이용한 알코올 제법 ··············· 180

  실험 5.2 ▶ Methylphenyl ether (Anisole)의 합성 · ········ 183

6 알데하이드와 케톤 · ···························· 187

  1. 카보닐기의 구조 ···························· 187

  2. 알데하이드 및 케톤의 제법 · ······················ 188

  3. 친핵성 아실 첨가 반응 ························· 189

  4. 물의 첨가 반응 · ···························· 189

  5. 알코올 첨가 반응 · ··························· 190

  6. 친핵성 첨가-제거 반응 · ························ 192

  7. 산화-환원 ······························· 193

  8. Grignard 시약과의 반응 ························ 195

  9. 케토-엔올 토토머화 ··························· 196

  10. 알돌 축합 반응 ···························· 196

  실험 6.1 ▶ Phenyl Magnesium Bromide 합성 ·········· 198

  실험 6.2 ▶ Diphenyl methyl carbinol 합성 ············· 201

  실험 6.3 ▶ Benzoic acid 합성 ···················· 205

  실험 6.4 ▶ 2-Furaldehyde의 semicarbazone의 제조 ······· 209

7 카복실산과 유도체 · ···························· 213

  1. 카복실산의 구조 및 성질 · ······················· 213

  2. 카복실산의 산성도 · ·························· 214

  3. 카복실산의 구조가 산성도에 미치는 영향 · ··············· 215

  4. 카복실산의 제법 ···························· 215

  5. 친핵성 아실 치환 반응 · ························ 216

  6. 카복실산 염의 형성 및 환원 ······················· 217

  7. 할로젠화 아실 화합물 ·························· 218

  8. 카복실산 무수물 ···························· 219

  9. 에스터의 합성: Fischer 에스터화 반응 · ··············· 220

  10. 락톤 ·································· 221

  11. 에스터의 가수분해와 가아민 분해 ··················· 221

  12. 에스터의 환원 반응 · ························· 222

  13. 에스터와 Grignard 시약의 반응 · ·················· 223

  14. Claisen 축합 반응 · ························· 224

  15. 아마이드 ······························· 225

  16. 나이트릴 · ······························ 226

  실험 7.1 ▶ Phenyl benzoate의 합성 · ··············· 227

  실험 7.2 ▶ 메틸 살리실레이트(methyl salicylate)의 비누화 반응 · ·· 231

8 다이아조늄 염의 형성 · ·························· 235

  실험 8.1 ▶ Methyl orange 합성(azo coupling) · ········· 237

9 유기 고분자 화학 · ····························· 241

  1. 축합 중합체 ······························· 241

  2. 첨가 중합체 ······························· 242

  실험 9.1 ▶ Polystyrene의 합성 · ·················· 243

  실험 9.2 ▶ 6,6-Nylon의 합성 ···················· 247

10 탄소-탄소 결합 형성 반응 ························· 251

  1. Suzuki 반응 ······························ 251

  2. Stille 반응 · ······························ 251

  3. Ullman 반응 ······························ 252

  4. Sonogashira 반응 · ························· 252

  5. Yamamoto 반응 ··························· 253

  실험 10.1 ▶ 2-phenylthiophene의 합성 ··············· 254

  실험 10.2 ▶ Bithiophene의 합성 ··················· 257

  실험 10.3 ▶ Phenyl-2-pyridine의 합성 · ·············· 261

  실험 10.4 ▶ 1,2-Diphenylethyne의 합성 · ············· 265