Synthesis of Cyclohexene E 2 6 Mechanism Mechanism

Synthesis of Cyclohexene (E 2반응) 수요일반 6조

Mechanism

Mechanism

Saytzeff’ s Rule (Zaitsev rule) - The more stable the alkene, the lower its heat of hydrogenation

Saytzeff’ s Rule (Zaitsev rule) - Hyperconjugation overlap between sigma bond orbital and pi-bond orbital or p-orbitals

Saytzeff’ s Rule (Zaitsev rule) ① ② ② ①

Saytzeff’ s Rule (Zaitsev rule) - Eliminations often favour the more stable trans-product over the cis-product

Hoffmann 생성물 - Hofmann rule The major alkene product is the least substituted and generally the least stable

Hoffmann 생성물 - Steric interactions (bulky base, substrate) +) potassium t-butoxide

Hoffmann 생성물 - The stereochemistry of the starting material can prevent the formation of the Zaitsev product

Zaitsev, Hoffmann Product

치환반응과 제거반응의 지배 요인 - Nucleophilic Solvent Substrate Leaving group

치환반응과 제거반응의 지배 요인 Solvent - 무극성 용매 - 극성 용매 protic solvent has a hydrogen atom bound to an oxygen or a nitrogen aprotic solvent

Sn 1과 E 1의 반응 비교 - Sn 1 and E 1 occur together - Increasing the temperature tends to increase the amount of elimination products produced

Mechanism (E 2)

실험기구 - 둥근 플라스크 분액깔때기 증류장치 Magetic stirrer/hot plate PH paper Stirring bar

실험결과 Cyclohexanol의 밀도 0. 962 g/ml Cyclohexanol의 부피 4 ml Cyclohexanol의 질량 3. 848 g Cyclohexanol의 분자량 100. 2 g/mol Cyclohexanol의 몰수 0. 038 mol 빈 플라스크의 무게 42. 741 g 빈 플라스크 + Cyclohexene 43. 342 g Cyclohexene의 무게(실험값) 0. 6 g Cyclohexene의 분자량 82. 14 g/mol Cyclohexene의 몰수 0. 038 mol Cyclohexene의 질량(이론값) 3. 121 g

실험결과 • 이론적 수득량 =cyclohexanol의 부피(ml) × cyclohexanol의 밀도 (g/ml)÷cyclohexanol의 분자량(g/mol) ×cyclohexene의 분자량(g/mol) =cyclohexene의 질량(g) • 수득률(%) =실험값/이론값 × 100% =0. 6 g/3. 121 g× 100% =0. 19%