CI neomenthyl chloride 2-menthene 25% 2-menthene 75% CI menthyl chloride 2-menthene only product 1) Why do neomenthyl chloride and menthyl chloride yield the products in the figure? 2) Why does menthyl chloride reacts 1/200 as quickly as neomenthyl chloride to produce the same product as neomenthyl chloride?

CI neomenthyl chloride 2-menthene 25% 2-menthene 75% CI menthyl chloride 2-menthene only product 1) Why do neomenthyl chloride and menthyl chloride yield the products in the figure? 2) Why does menthyl chloride reacts 1/200 as quickly as neomenthyl chloride to produce the same product as neomenthyl chloride?

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter11: Ethers, Epoxides, And Sulfides

Section11.9: Reactions Of Epoxides

Problem DQ

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why the reaction of 2-bromopropane withNaOCOCH3 gives (CH3)2CHOCOCH3 exclusively as product, but the reactionof 2-bromopropane with NaOCH2CH3 gives a mixture of (CH3)2CHOCH2CH3(20%) and CH3CH=CH2 (80%)
Explain why the reaction of 2-bromopropane with NaOCOCH3 gives(CH3)2CHOCOCH3 exclusively as product, but the reaction of 2-bromopropane with NaOCH2CH3 gives a mixture of (CH3)2CHOCH2CH3(20%) and CH3CH=CH2 (80%).
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Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides. One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(CzHs)3). 3SnCl4 + 4Al(C2H5)3 → 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.160 L of SnCl4 (d= 2.226 g/mL) was treated with 0.346 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). What is the theoretical yield in this experiment (mass of tetraethylstannane, Sn(C2H5)4)? If 0.257L of tetraethylstannane (d= 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?
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Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides.One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(C2H5)3). 3SnCl4 + 4Al(C2H5)3 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.230 L of SnCl4 (d = 2.226 g/mL) was treated with 0.396 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). If 0.335 L of tetraethylstannane (d = 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?
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A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an SN2 displacement, which takes place with inversion of configuration. He ordered a bottle of (S)-butan-2-ol for his chiral starting material. He also remembered that the SN2 goes best on primary halides and tosylates, so he made ethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane. What would have been the best synthesis of (R)-2-ethoxybutane?
A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an SN2 displacement, which takes place with inversion of configuration. He ordered a bottle of (S)-butan-2-ol for his chiral starting material. He also remembered that the SN2 goes best on primary halides and tosylates, so he made ethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane. What enantiomer of 2-ethoxybutane did he obtain? Explain how this enantiomer results from the SN2 reaction of ethyl tosylate with sodium (S)-but-2-oxide.
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