[기출문제] 호서대 아산캠퍼스 유기화학 2023-2 중간 기출문제 (정답 포함)

1. b-elimination

1-1. IUPAC name

1-2. β-elimination → products

1-3. (더 안전한 생성물을 고르시오)

2. (R)-2-bromobutane → SN2 reaction (with inversion of configuration at the stereocenter)

3. Competition between the E2 and SN2 reactions

4. 3-bromo-2-methyl-2-butanol + NaOH → epoxide

1. b-elimination
9.1(B) p. 268
1-1. IUPAC name
2-bromo-2,3-dimethylbutane
1-2. b-elimination → products
2,3-dimethyl-2-butene 2,3-dimethyl-1-butene
1-3. 2,3-dimethyl-2-butene
이중결합이 안쪽에 있는 화합물이 안정성이 높아서 더 많이 생성된다.
2. (R)-2-bromobutane → SN2 reaction (with inversion of configuration at the stereocenter)
9.4(C) p. 277
C2H5
(R)-2-bromobutane → (S)-2-butanol
HOSEO UNIVERSITY
Chemical Engineering
KJB
2023 Midterm Exam (Organic Chemistry II)
2023. 10. 19
3. Competition between the E2 and SN2 reactions
9.5(G) pp. 295~296
β 탄소의 알킬 치환기 영향
→ 제거반응 증가
bromoethane
bromopropane 1-bromo-2-methylpropane
4. 3-bromo-2-methyl-2-butanol + NaOH → epoxide
1
2
3
3
2
1
2,2,3-trimethyloxirane
3번 탄소 = chiral
(답)
11.3(B) p. 379
1
3
1-bromo-2,2-dimethylpropane
β 수소가 없어서 E2반응은 일어나지 않음
1
1
3
3
2
2
2
CH3
H
(3S)-2,2,3-trimethyloxirane (3R)-2,2,3-trimethyloxirane