Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 12, Problem 6PP
PRACTICE PROBLEM 12.4
Predict the products of the following acid–base reactions. Using
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HO
CH30 Na
A
+
B
O,N
pK =7
(a) Provide structures for A and B (including nonbonding electron pairs and formal
charges where necessary), where A is the conjugate acid and B is the conjugate base
of the reaction.
Answer:
(b) Provide and arrow pushing mechanism to show how A and B are formed.
Answer:
(c) Will the reaction proceed from left to right (i.e. are A and B favoured at equilibrium)?
Explain your answer.
Answer:
(d) Draw all important resonance contributors of the conjugate base B. Rank the
contributors from most stable to least stable (if contributors are equally stable indicate
this with an equals sign)
Arrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenol
H3C.
OH
HO Na
+
pK = 9
(a) Provide structures for A and B (including nonbonding electron pairs and formal
charges where necessary), where A is the conjugate acid and B is the conjugate base
of the reaction.
Answer:
(b) Provide and arrow pushing mechanism to show how A and B are formed.
Answer:
(c) Will the reaction proceed from left to right (i.e. are A and B favoured at equilibrium)?
Explain your answer.
Answer:
(d) Draw all important resonance contributors of the conjugate base B.
Chapter 12 Solutions
Organic Chemistry
Ch. 12 - Prob. 3PPCh. 12 - PRACTICE PROBLEM Assign oxidation states to each...Ch. 12 - Prob. 2PPCh. 12 - PRACTICE PROBLEM
12.4 What oxidation product would...Ch. 12 - Prob. 5PPCh. 12 - PRACTICE PROBLEM 12.4 Predict the products of the...Ch. 12 - Prob. 7PPCh. 12 - Prob. 8PPCh. 12 - Practice Problem 12.7
Provide retrosynthetic...Ch. 12 - Prob. 10PP
Ch. 12 - What products would you expect from the reaction...Ch. 12 - What products would you expect from the reaction...Ch. 12 - What product (or products) would be formed from...Ch. 12 - Prob. 14PCh. 12 - 12.13 Write reaction conditions and the product...Ch. 12 - Prob. 16PCh. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the major organic product from each of the...Ch. 12 - 12.21 Predict the major organic product from each...Ch. 12 - 12.22 Predict the product of the following...Ch. 12 - Synthesize each of the following compounds from...Ch. 12 - Prob. 24PCh. 12 - 21. Write a mechanism for the following reaction....Ch. 12 - Prob. 26PCh. 12 - Prob. 27PCh. 12 - 23. What organic products A-H would you expect...Ch. 12 - Prob. 29PCh. 12 - Show how 1-pentanol could be transformed into each...Ch. 12 - Provide the reagents needed to accomplish...Ch. 12 - Prob. 32PCh. 12 - For each of the following alcohols, write a...Ch. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - 34. Synthesize the following compound using...Ch. 12 - 37. Explain how and IR spectroscopy could be used...Ch. 12 - 12.40
When sucrose (common table sugar) is treated...Ch. 12 - 38. An unknown X shows a broad absorption band in...Ch. 12 - Prob. 1LGPCh. 12 - Which of the following could be employed to...Ch. 12 - Prob. 2QCh. 12 - 12.3 Supply the missing reagents.
Ch. 12 - 12.4 Supply the missing reagents and...Ch. 12 - Supply the missing starting compound.
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- (a) Rank the following compounds in order of increasing acidity. (b) Which compound forms the strongest conjugate base?arrow_forward(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_forwardDraw the product of the following Lewis acid-base reaction. Discuss whether the product will retain its monomeric form or if it will dimerise and why. (c) Ph Toluene AICI CHO Pharrow_forward
- 5. The structure of anthocyanin, a naturally occurring compound that acts as a pigment in many fruits and vegetables, is given below. At low pH values (<3), it exists as the cation shown below and exhibits a bright red color. At higher pH values (-7), it exhibits a purple-ish color, indicating a shift to a longer wavelength absorption in the UV-visible spectrum. As the pH is raised from pH 3 to pH 7, one of the hydroxyl groups can be deprotonated (the H that is removed has been circled for you) to produce the corresponding resonance stabilized neutral compound. Draw the two most stable Lewis octet resonance structures for this anthocyanin at pH 7. Make sure to explicitly show all non-bonding lone pairs and formal charges where appropriate. Include curved arrows to show how you got from the first resonance structure to the other. 5. :: :: HO 0:0 : ÖH :O: -[sugar] anthocyanidin structure at pH 3 red color compound (H+) first structure here second structure here 1 -arrow_forwardPredict the products of the following reactions.arrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 836 Ph THF A 1 B H₂SO4 100 °C 3 OH Which of the two methods (A or B) is more likely give high yield of methylenecyclohexane 2? Briefly explain.arrow_forward
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- 16.55 Working backwards, deduce the starting material that led to the indicated product through the defined reactions. (1) MsCl, pyr (2) KCN, DMF (a) A (1) (a) NaH; (b) HCOCH 3 (2) mCPBA (3) MeMgBr; H3O+ (4) NaH, Mel OMe X (b) B (3) MeMgBr; H₂O+ (4) H₂NNH₂, cat. HA (5) KOH, Aarrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) Ph THF A Ph Ph B H₂SO4 100 °C 3 OH (iii) In analysing both these methods, are there other possible alkene products other than methylenecyclohexane 2? Use mechanistic details to support your answer.arrow_forwardPlease name the structure, thanksarrow_forward
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