Following are structural formulas for phenol and cyclohexanol along with the acid dis- sociation constants for each. OH НО Cyclohexanol pK, 18 Phenol pK, 9.96 Propose an explanation for the fact that phenol is a considerably stronger acid than cyclohexanol.

Following are structural formulas for phenol and cyclohexanol along with the acid dis- sociation constants for each. OH НО Cyclohexanol pK, 18 Phenol pK, 9.96 Propose an explanation for the fact that phenol is a considerably stronger acid than cyclohexanol.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Related questions

Q: Choose the most appropriate name for the follow OH 11 3-ethyl -1- hydroxyl pentanal 3-ethyl…

A: Choose the most appropriate name for the following compound:

Q: If 1g of Phenol is dissolved in 1L of water in a flask labelled flask A, then 10ml of solution in…

A: The objective of this question is to find the concentration of the solution in flask B after a…

Q: Show the structures of the missing substance(s) in each of the following acid-base equilibria. CH3…

A: According to Bronsted-Lowry concept, the acidic and basic character of a compound can be interpreted…

Q: Answer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D…

A: We are given the pKa values of benzoic acid = 4.2 and ethanol = 16.

Q: Although p-hydroxybenzoic acid is less acidic than benzoic acid, o-hydroxybenzoic acid is slightly…

A: The ability of compounds to give the proton or H+ is called acidity. Acidic compound forms the more…

Q: Arrange the following in order of DECREASING boiling point. 1 is highest, 5 is lowest.…

A: The boiling point of a compound is determined by the strength of the intermolecular forces between…

Q: Arrange the following substances according to their increasing acidity a) c) Fenol,…

A: The objective of the question is to arrange the given substances in the order of their increasing…

Q: Carbonyl compounds can be protonated on the carbonyl oxygen. Explain why propanoic acid is more…

A: Wherever the electron cloud is present in higher density protonation takes place very swiftly.

Q: Which of the following is the correct set of arrows when isopropanol reacts with acetylide in…

Q: Rank the following compounds in order of increasing acidity, and explain in detail your choice of…

A: NO2 is an electron withdrawing group and it is bonded directly to benzene ring which further is…

Q: Predict which compound of each pair will be more acidic. Draw the structures and explain your…

A: Answer:- This question is answered by using the simple concept of determination of acidic strength…

Q: CH3 NO2 NH2 CH3 NH2 N' NH2

A: A base is defined as a molecule that has the ability to donate an electron pair .

Q: Answer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D…

Q: Using molecular structures, what will happen in the following situations: 1) Benzoic acid is…

A: Benzoic acid is insoluble in water but soluble in diethyl ether.

Q: Identify the functional groups in each constitutional isomer of C,H,NO. Select all that apply Isomer…

A: Question 1: The functional group is amine.An amine is a compound with a nitrogen atom attached to a…

Q: Phenol has a pka = 10.0. 4-Hydroxybenzaldehyde has a pK, = 7.3. Draw resonance forms of the…

A: Concept of Resonance; When all the properties of a molecule cannot be explained by a single…

Q: Which of the following statements is INCORRECT concerning the two acids below? Options: Acetic…

Q: How many kinds of chemically non-equivalent carbons are there in each of the following compounds? a…

A: The objective of the question is to find the kinds (numbers) of non-equivalent carbons in the given…

Q: The major reason that phenol is a more acidic than cyclohexanol is It is a better proton donor The…

Q: 4-Methylphenol is more acidic than ethanol (pKa 10.36 vs 16.0) , even though both contain an OH…

A: The organic compounds containing -OH group are slightly acidic in nature. The acidic properties of…

Q: COOH O 3-carboxytoluene O 3-methylcyclohexanecarboxylic acid O m-methylbenzoic acid O…

A: There is Cyclohexane ring in the compound. Now one carboxyl group and one methyl group is attached…

Q: 4 5 Arrange the following bases in increasing base strength. There is no partial credit on this…

A: The relative strength of acids depends on their Ka (acid dissociation constant) values. The higher…

Q: Show the structures of the missing substance(s) in each of the following acid-base equilibria. CH3H2…

A: missing structure in the below reaction needs to be drawn:

Q: 1) Different carboxylic acid derivatives react at different rates. Consider reaction below using one…

A: Step 1: The order of leaving approach of the functional groups given here is : -Cl >…

Q: The order of increasing acidity is Phenol < meta-cyanophenol < ortho-cyanophenol 1.how about…

A: Given that The order of increasing acidity is Phenol < meta-cyanophenol < ortho-cyanophenol…

Q: Write out a chemical equation (draw bond-line structure) for the reaction between p-bromoaniline…

A: The structure of the given reactant p-bromoaniline appears as follows: The chemical formula of the…

Q: which two of the following will react with weak base; sodium bicarbonate and which two will react…

A: Given question related to the distinguishion of organic compounds by some chemical reactions.

Q: identifying letters A-D below each structure. A table of pka values for various organic and…

A: Given : We have to write which of the following is weaker acid and its conjugate acid .

Question

Following are structural formulas for phenol and cyclohexanol along with the acid dis-
sociation constants for each.
OH
НО
Cyclohexanol
pK, 18
Phenol
pK, 9.96
Propose an explanation for the fact that phenol is a considerably stronger acid than
cyclohexanol.

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 2 images

SEE SOLUTION Check out a sample Q&A here

Similar questions

One acid–base classification defines a base as a substance that acts as a proton (H+H+) acceptor, and is also known as a Bronsted–Lowry base. All bases contain a non‑bonding pair of electrons. In each of the molecules, identify the atom that behaves only like a Bronsted–Lowry base. The atom in compound A that behaves only like a Bronsted–Lowry base is the nitrogen. the oxygen on the carbonyl. the oxygen bonded to hydrogen. the hydrogen bonded to oxygen.
Give detailed Solution with explanation needed..don't give Handwritten answer
Amines are weak bases. Table 10.2 in the course textbook provides a list of pKb values for several amines. The pK values for three amines and their structures are shown below. Explain why increased substitution on nitrogen results in an increase of the pKb value. H3C-NH2 PK = 3.36 H3C N-H pKb = 3.27 H₂C' H3C N-CH3 PK = 4.19 H₂C
what is the 1UPAC Neme tos the fullwing Malecole? OH 1. 8-Ethyl- S-hydronyhexenal 2. 3- E thylhenanal - 3-01 g 4- E thyl -2-hydroxyhevanal 4- Ethyl-2-hydroxpentamel 5. Nave of these
What could be used as a replacement for phosphoric acid as a catalyst for the dehydration of cyclohexanol? Assume you want to avoid SN1 side reactions as much as possible. Sodium chloride Hydrobromic acid Sulfuric acid Hydrochloric acid
In the following pairs of compounds, which is the most acidic? Benzoic acid and 4-nitrobenzoic acid p-Nitrophenol and m-nitrophenol 4-Methylbenzoic acid and 4-chlorobenzoic acid
Indicate which is more acidic: 4-nitrophenol or 4-chlorophenol. Explain the reason.
Phenol (hydroxybenzene) behaves as a weak acid. a) Write out the equilibrium equation for its partial dissociation in water. b) Write out the expression for the acid dissociation constant, Ka. d) Draw the conjugate base of phenol and show how it is stabilised by resonance. e) Compare and explain the acidity of phenol (p = 9.9) with that of: cyclohexanol (pk = 16.0) 3-fluorophenol (pK₁ = 9.3) 4-acetylphenol (pK, = 8.1)
None
How would you describe the reaction between NaOH (a base) and the mixture of benzoic acid and methyl benzoate? Both react with NaOH because bases accept protons Neither react with NaOH because neither has an acidic proton Benzoic acid reacts with NaOH because it has an acidic proton, but methylbenzoate does not Methyl benzoate reacts with NaOH because it has an acidic proton, but benzoic acid does not