A different product is formed in each of the following reactions. Identify the p

Question

A different product is formed in each of the following reactions. Identify the product in each case from their 1H NMR spectra below, and suggest an explanation for the observed regioselectivity. Please answer all portions.

Be sure to answer all parts. A different product is formed in each of the following reactions. Identify the product in each case from their H NMR spectra below, and suggest an explanation for the observed regioselectivity. Compound ARGHuo) 4,0 3,5 Chemicalshift ppm Lui H2C-CHCH, 1. diethyl ether Compound A: C9H120 2. H30 Compound A is: Phenyl-1-propanol o l-Phenyl-2-propane 1-Phenyl-1-propanol o 2-Phenyl-2-propane The observed regioselectivity in compound A is explained by: O Phenyllithium attacks only the epoxide methine carbon. O Phenyllithium attacks both methylene and methine epoxide carbons. O Phenyllithium is too sterically hindered to react. O Phenyllithium attacks only the epoxide ene carbon. Compound B Chemical a ppm l. diethyl ether CH Li Compound B: C9H120 2. H30 Compound B is: o Phenyl-1-propane 1-Pheny -propanol o henyl-1-propanol Pheny -propanol The observed regioselectivity in compound B is explained by O Methyllithium is too lly hindered to react. O Methyllithium attacks only the epoxide methine carbon. O Methyllithium attacks both methylene and methine epoxide carbons. O Methyllithium attacks only the epoxide methylene carbon.

Explanation / Answer

First reaction,

phenyl lithium + epoxide

Formula = C9H12O

degree of unsaturation = 4

Structure of product A,

1-phenyl-2-propanol

The observed regioselectivity of product A is due to,

Phenyl lithium only attacks the methylene carbon of epoxide

---

Compound B

Structure of compound B,

1-phenyl-1-propanol

The observed regioselectivity seen for compound B is,

methyl lithium attacks only the methylene carbon of epoxide

Related Questions

Navigate

• Browse (All)
• Browse A
• Subjects

---

---

Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.