The observation that p-nitrobenzyl alcohol is more acidic than benzyl alcohol but p-methoxybenzyl alcohol is less acidic is to be explained. Concept introduction: Alcohols are acidic because the alkoxide ion formed due to loss of H + is stabilized by solvation. Aromatic alcohols with electron releasing substituent groups on the ring are less acidic and those with electron attracting substituent groups are more acidic. To explain: The observation that p-nitrobenzyl alcohol is more acidic than benzyl alcohol but p-methoxybenzyl alcohol is less acidic.

Question

When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone, why

Answer 1

Question

Chapter 17.2, Problem 5P

Interpretation Introduction

Interpretation:

The observation that p-nitrobenzyl alcohol is more acidic than benzyl alcohol but p-methoxybenzyl alcohol is less acidic is to be explained.

Concept introduction:

Alcohols are acidic because the alkoxide ion formed due to loss of H⁺ is stabilized by solvation. Aromatic alcohols with electron releasing substituent groups on the ring are less acidic and those with electron attracting substituent groups are more acidic.

To explain:

The observation that p-nitrobenzyl alcohol is more acidic than benzyl alcohol but p-methoxybenzyl alcohol is less acidic.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone, why

Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l). The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 8.50 gof butanoic acid and excess ethanol? Express your answer in grams to three significant figures.

Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) a) Given 7.70 g of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100% yield? b) A chemist ran the reaction and obtained 5.25 g of ethyl butyrate. What was the percent yield? c) The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.70 g of butanoic acid and excess ethanol?