In acid-base equilibria, the presence of an electron withdrawingsubstituent on the R- group of the alcohols increase the acidity of thealcoholby stabilizing the ROH groupby decreasing the stability of the RO- groupby increasing the stability of the RO- groupdecreasing the stability of the ROH group

The nature of alcohols (R-OH) is acidic. After the removal of proton (deprotonation), alcohol forms…

Answered: In acid-base equilibria, the presence…

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

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.49P

See similar textbooks

Similar questions

Using your knowledge of general chemistry and organic chemistry, answer the following questions: Predict the relative acidities within each of the following groups, then identify the conjugate bases, and finally predict their relative leaving group abilities HClO3 and HClO2 PH3 and H2S [NH4]+ and [H3O]+ Explain why the trifluoromethane sulfonate (TfO-) ion is a better leaving group than the methanesulfonate (MsO-) ion.
Explain this statement: Although 2-methoxyacetic acid (CH3OCH2COOH) is a stronger acid than acetic acid (CH3COOH), p-methoxybenzoic acid (CH3OC6H4COOH) is a weaker acid than benzoic acid (C6H5COOH).
Explain this statement: Although 2-methoxyacetic acid (CH3OCH2COOH)is a stronger acid than acetic acid (CH3COOH), p-methoxybenzoic acid(CH3OC6H4COOH) is a weaker acid than benzoic acid (C6H5COOH).
Explain the following behaviours :(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses.(ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol.
When a primary alcohol is treated with p-toluenesulfonyl chloride at room temperature in the presence of an organic base such as pyridine, a tosylate is formed. When the same reaction is carried out at higher temperature, an alkyl chloride is often formed. Explain.
Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic acid have no tetrahedral chiral center, and yet they can be resolved to a pair of enantiomers. Account for this chirality.
Arrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.
(a) Arrange the following compounds in an increasing order of their indicated property :(i) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength)(ii) CH3CH2CH (Br) COOH, CH3CH (Br) CH2COOH,(CH3)2CHCOOH, CH3CH2CH2COOH (acid strength)(b) How would you bring about the following conversions :(i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde(iii) Bromobenzene to 1-phenylethanol
Arrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenol
#B: Methyl acetate has methoxy, -OCH3 as the remaining of the alcohol part in the ester. Isopropyl acetate has isopropoxy, -OCH(CH3)2 as the remaining of the alcohol part in the ester. -OCH(CH3)2 is more electron donating than the methoxy, -OCH3 group due to the presence of two electron-donating -CH3 group in the former. Hence saponification reaction of Isopropyl acetate is much slower than methyl acetate. Hence the rate of saponification of methyl acetate, CH3CCO2CH3 is 50 times greater than that for isopropyl acetate.
Explain WHY/HOW all please - Propanol CANNOT protonate ethylamine - 3-methylheptan-3-ol CANNOT be produced from the reaction of an ester with a Grignard reagent - Carbonic acid is dissolved in water, the equilibrium of its dissociation will have a Keq value = between 0 and 1 - Pentane is less soluble in water than octane - Dehydration of pentan-2-ol to produce pent-2-ene which involves heating: values of Keq = between 0 and 1 and ΔG = > 0 - The molecule cis-1-ethyl-3-iodocyclohexane CANNOT adopt a chair conformation in which there are no equatorial groups.
Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.

SEE MORE QUESTIONS

Recommended textbooks for you

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

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

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

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

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

SEE MORE TEXTBOOKS