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Concept explainers
(a)
Interpretation:
The phenol derivative which is more acidic among
Concept introduction:
The acidic strength of the phenol molecule is dependent on the stabilization of the phenoxide ion formed after the dissociation of the proton. The phenoxide ion is stabilized by the resonance effect. The phenoxide is more stabilized by the
(b)
Interpretation:
The phenol derivative which is more acidic among phenol and
Concept introduction:
The acidic strength of the phenol molecule is dependent on the stabilization of the phenoxide ion formed after the dissociation of the proton. The phenoxide ion is stabilized by the resonance effect. The phenoxide is more stabilized by the
(c)
Interpretation:
The phenol derivative which is more acidic among
Concept introduction:
The acidic strength of the phenol molecule is dependent on the stabilization of the phenoxide ion formed after the dissociation of the proton. The phenoxide ion is stabilized by the resonance effect. The phenoxide is more stabilized by the
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Chapter 18 Solutions
EBK ORGANIC CHEMISTRY
- (c) Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluorophenol.arrow_forward- Rank the following substances in order of increasing acidity: (a) Phenol, p-methylphenol, p-(trifluoromethyl)phenol (b) Benzyl alcohol, phenol, p-hydroxybenzoic acidarrow_forwardPredict which member of each pair is more acidic, and explain the reasons for your predictions.(a) cyclopentanol or 3-chlorophenol (b) cyclohexanol or cyclohexanethiol(c) cyclohexanol or cyclohexanecarboxylic acid (d) butan-1-ol or 2,2-dichlorobutan-1-olarrow_forward
- Arrange each group of compounds in order of increasing acidity.(b) p-toluenesulfonic acid, acetic acid, chloroacetic acidarrow_forwardPredict which member of each pair is more acidic, and explain the reasons for your predictions.(a) cyclopentanol or 3-chlorophenolarrow_forwardArrange each group of compounds in order of increasing acidity.(c) benzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acidarrow_forward
- Predict which member of each pair will be more acidic. Explain your answers.(a) methanol or tert-butyl alcohol(b) 2-chloropropan-1-ol or 3-chloropropan-1-ol(c) 2-chloroethanol or 2,2-dichloroethanol(d) 2,2-dichloropropan-1-ol or 2,2-difluoropropan-1-olarrow_forwardArrange each group of compounds in order of increasing basicity.(a) CH3COO-, ClCH2COO-, and PhO- (b) sodium acetylide, sodium amide, and sodium acetate(c) sodium benzoate, sodium ethoxide, and sodium phenoxide (d) pyridine, sodium ethoxide, and sodium acetatearrow_forward(a) Which of the following will NOT produce a carboxylic acid or carboxylate ion? 1-butanol + H2CrO4 2-butene + O3/H2O2 butanal + PCC butanal + H2CrO4 (b) Which of the following will NOT produce a carboxylic acid or carboxylate ion? 1-butanol + H2CrO4 2-butene + O3/H2O2 butanal + PCC butanal + H2CrO4arrow_forward
- The cis ketone A is isomerized to a trans ketone B with aqueous NaOH. A similar isomerization does not occur with ketone C. (a) Draw the structure of B using a chair cyclohexane. (b) Label the substituents in C as cis or trans, and explain the difference in reactivity.arrow_forward(A) Which of the following ethers is the least soluble in water? (B) Which produces ethanol and methyl iodide after treatment with dilute HI?arrow_forwardExplain the following statements. You must use chemical equations to justify your explanation. (ii) (I) Phenol is more acidic than cyclohexanol.arrow_forward
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