Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 16.SE, Problem 76AP
Interpretation Introduction
Interpretation:
Whether p-methylphenol is more acidic or less acidic than unsubstituted phenol is to be explained.
Concept introduction:
Phenols with electron releasing substituents attached to the ring are less acidic than phenol while phenols with electron withdrawing substituents attached to the ring are more acidic than phenol.
To explain:
Whether p-methylphenol is more acidic or less acidic than unsubstituted phenol.
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OChem help with IUPAC names involving Ph and Bn
The phenyl group (Ph-R, C6H5-R) can be formed by removing a hydrogen from benzene and attaching a substituent to where the hydrogen was removed.
The benzyl group (abbv. Bn), similar to the phenyl group, is formed by manipulating the benzene ring. In the case of the benzyl group, it is formed by taking the phenyl group and adding a CH2 group to where the hydrogen was removed. Its molecular fragment can be written as C6H5CH2-R, PhCH2-R, or Bn-R.
Please provide the IUPAC name for the following:
(Ph)2CHC(CH3)2CC(CH2)3CH(Bn)CHO
Rank the following compounds in their correct order of acidity. 1=Most acidic and 4=least acidic.
State whether the following reactions are favorable or unfavorable. Explain the reason behind your answer.
Chapter 16 Solutions
Organic Chemistry
Ch. 16.1 - Prob. 1PCh. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SŪ4. deuterium...Ch. 16.3 - Prob. 5PCh. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P
Ch. 16.4 - Prob. 11PCh. 16.4 - Acetanilide is less reactive than aniline toward...Ch. 16.4 - Prob. 13PCh. 16.5 - At what position would you expect electrophilic...Ch. 16.5 - Show the major product(s) from reaction of the...Ch. 16.6 - The herbicide oxyfluorfen can be prepared by...Ch. 16.7 - Treatment of p-bromotoluene with NaOH at 300°C...Ch. 16.8 - Prob. 18PCh. 16.8 - Prob. 19PCh. 16.8 - Prob. 20PCh. 16.9 - Prob. 21PCh. 16.10 - Prob. 22PCh. 16.10 - Prob. 23PCh. 16.SE - Prob. 24VCCh. 16.SE - The following molecular model of a...Ch. 16.SE - Prob. 26VCCh. 16.SE - Prob. 27VCCh. 16.SE - Aromatic iodination can be carried out with a...Ch. 16.SE - Prob. 29MPCh. 16.SE - The carbocation electrophile in a Friede1-Crafts...Ch. 16.SE - Prob. 31MPCh. 16.SE - The nitroso group, —N=O, is one of the few...Ch. 16.SE - Triphenylmethane can be prepared by reaction of...Ch. 16.SE - Using resonance structures of the intermediates,...Ch. 16.SE - Benzene and alkyl -substituted benzenes can be...Ch. 16.SE - Prob. 36MPCh. 16.SE - Hexachlorophene, a substance used in the...Ch. 16.SE - Benzenediazonium carboxylate decomposes when...Ch. 16.SE - 4-Chloropyridine undergoes reaction with...Ch. 16.SE - Propose a mechanism to account for the following...Ch. 16.SE - In the Gatterman-Kochreaction, a formyl group...Ch. 16.SE - Treatment of p-tert-butylphenol with a strong acid...Ch. 16.SE - Benzyl bromide is converted into benzaldehyde by...Ch. 16.SE - Prob. 44MPCh. 16.SE - Prob. 45MPCh. 16.SE - Prob. 46APCh. 16.SE - Prob. 47APCh. 16.SE - Prob. 48APCh. 16.SE - Predict the major monoalkylation products you...Ch. 16.SE - Name and draw the major product(s) of...Ch. 16.SE - Prob. 51APCh. 16.SE - Prob. 52APCh. 16.SE - What product(s) would you expect to obtain from...Ch. 16.SE - Prob. 54APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 56APCh. 16.SE - Prob. 57APCh. 16.SE - Prob. 58APCh. 16.SE - Prob. 59APCh. 16.SE - Prob. 60APCh. 16.SE - Prob. 61APCh. 16.SE - Prob. 62APCh. 16.SE - Prob. 63APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 65APCh. 16.SE - Prob. 66APCh. 16.SE - Draw resonance structures of the intermediate...Ch. 16.SE - Prob. 68APCh. 16.SE - p-Bromotoluene reacts with potassium amide to give...Ch. 16.SE - Prob. 70APCh. 16.SE - Prob. 71APCh. 16.SE - Prob. 72APCh. 16.SE - Use your knowledge of directing effects, along...Ch. 16.SE - Identify the reagents represented by the letters...Ch. 16.SE - Phenols (ArOH) are relatively acidic, and the...Ch. 16.SE - Prob. 76APCh. 16.SE - Prob. 77APCh. 16.SE - Melamine, used as a fire retardant and a component...
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- Explain some carboxylic acids in order of decreasing reactivity?arrow_forwardIndicate which is more acidic: 4-nitrophenol or 4-chlorophenol. Explain the reason.arrow_forwardIndicate the products A and B that are obtained in the following reactions: OH CH3 + HOCH2-CH₂OH + TSOH → A 1° NaH/THF A + →> B 2º C6H5-CH2Cl Briefly comment on each reaction.arrow_forward
- Which is more acidic, p-methylphenol or phenol? why? Why is water more acidic than ethanol but slightly less acidic than methanol? Explain the acidity trend of alcohols: 1>2 > 3arrow_forwardArrange the following types in order of increasing acidity: carboxylic acids, alcohols, phenols, water. Explain why.arrow_forwardb) Compounds in which the –OH of the carboxyl group is replaced by certain other groups are called carboxylic acid derivatives. The most important of which are acyl halides, acid anhydrides, esters and amides. Discuss the relationship between carboxylic acid, acid chloride and acid anhydridearrow_forward
- Provide the reagents necessary to complete the following reactions. More than one step may be necessary, if so number separate steps.arrow_forwardThe pKa of phenol is 10.0 and the pKa of para-nitrophenol is 7.2. Given this information, one knows that The conjugate base of para-nitrophenol must be less stable than the conjugate base of phenol The conjugate acid of para-nitrophenol must be more stable than the conjugate base of phenol The conjugate base of para-nitrophenol must be more stable than the conjugate base of phenol Both acids are basesarrow_forwardArrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.arrow_forward
- Two methods convert an alkyl halide into a carboxylic acid having one more carbon atom. (1] R-X + "CN R-CN R,COOH COOH (Section 22.18) + X- new C-C bond [1] CO2 RCOOH (Section 20.14) [2] H3O [2] R-X + Mg R-MgX Depending on the structure of the alkyl halide, one or both of these methods may be employed. For each alkyl halide, write out a stepwise sequence that converts it to a carboxylic acid with one more carbon atom. If both methods work, draw both routes. If one method cannot be used, state why it can't. Br a. CH,CI b. c. (CH3)3CCI d. HOCH,CH,CH,CH,Brarrow_forwardCyclohexane-1,3-dione is a diketone that can act as a Brønsted-Lowry acid despite not having a hydrogen bonded to an electronegative atom. In this molecule, a hydrogen bonded to carbon 2 is acidic. Hexanol is an alcohol and hence can also act as a Brønsted-Lowry acid. a) Draw the stabilized conjugate bases of cyclohexane-1,3-dione and hexanol. No need to draw the protonated forms. b) Based on your illustration in part (a), predict which one has a lower pKa between cyclohexane-1,3-dione and hexanol. Explain why.arrow_forwardWhich of the following carboxylic acids has the highest solubility in water? A) CH₃CH₂C(=O)OH B) CH₃CH₂CH₂CH₂C(=O)OH C) CH₃(CH₂)₅C(=O)OH D) CH₃(CH₂)₁₀C(=O)OH E) All of these have equal solubility.arrow_forward
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