Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 22.SE, Problem 19VC
Interpretation Introduction
Interpretation:
The most acidic hydrogen in the structure represented by the model is to be identified. Further whether it is axial or equatorial also is to be stated.
Concept introduction:
The most acidic hydrogen is one whose p orbital, after the removal of hydrogen, remains aligned such that optimum overlap with the π electrons of the carbonyl oxygen is possible.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
HSO4- is the conjugate
of H2SO4 and the conjugate
of SO,2-
• View Available Hint(s)
O acid / acid
O acid / base
O base / acid
O base / base
Submit
Which of the following best describes the lone pairs on oxygen in the following aromatic molecule. The two lone pairs on oxygen are not shown in the picture
below.
0
One lone pair on oxygen is in an sp² orbital and the other is an unhybridized p-orbital and participates in aromaticity.
O Both lone pairs on oxygen are in an sp3 orbitals and can't participate in aromaticity.
O Both lone pairs on oxygen are in unhybridized p-orbitals and both participate in aromaticity.
O The lone pairs of oxygen have nothing to do with this compound being aromatic.
Click the "draw structure" button to launch the drawing utility.
Under certain reaction conditions, 2,3-dibromobutane reacts with two equivalents of base to give three
products, each of which contains two new T bonds. Product A has two sp hybridized carbon atoms,
product B has one sp hybridized carbon atom, and product C has none. What is the structure of C?
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Terminal alkyne is considered a more acidic compound because it has a lower s character. True or Falsearrow_forwardCH3)3CO- is a base that can be made from (CH3)3COH (pKa = 18). Using curved arrow formalism, draw a reaction of this base reacting with NH3 (pKa = 36). Show the products. Which way will be equilibrium lie?arrow_forward4. For each of the following sets of compounds, circle the most acidic compound and put a box around the least acidic compound. Note: (a) (b) (c) (d) Ph-- = CICH₂CO₂H Ph-OH Ph-SH CH3CH₂NH2 CH3CO₂H Ph-CH₂OH Ph-OH CH3CH₂NH3+ Cl3CCO₂H CH3(CH₂)2SH Ph-NH, BrCH₂NH₂arrow_forward
- Rank the following in order of increasing basicity. соо coo" coo .cooarrow_forwardNaNH2 is typically used instead of KOH to produce alkynes through elimination because NaNH2 is a stronger base. Explain why KOH can be used to create diphenylacetylene.arrow_forward5. Draw the structures of A and B, and use the curved arrow formalism to show the Trensproduct is med bond making and bond breaking that occurs in the formation of A and B through the following series of reactions. Note: Sodium hydride (NaH) is a strong base. NaH A diethylether Use the curved arrow formalism to show the bond meliarrow_forward
- Curved arrows are used to illustrate the flow of electrons. Using the provided resonance structures, draw the curved electron- pushing arrows to show the interconversion between resonance hybrid contributors. Be sure to account for all bond- breaking and bond-making steps. I I I I :O: farrow_forwardIs the hydroxyl group on ring A axial or equatorial?arrow_forwardWhen we have discussed the enol-keto tautomerization of ketones in class, the isomerization has been facililated by an acid or base catalyst, with most ketones heavily favoring the carbonyl isomer at equilibrium. However, samples of the ketone below in its pure form (with no acid, base or water present) contain nearly 10% of the enol form! OH -90% -10% From this data, we can infer that the enol isomer of this ketone is particularly stable. Explain the stability of this enol, using terms and ideas that we have discussed in this unit.arrow_forward
- What is the configuration of the double bond in each of the following compounds (E, Z, or neither)?arrow_forwardHeteroaromatic Structures Aromatic compounds which contain non-carbon atoms (e.g., O, N, S) as part of the cyclic conjugated a system are called heteroaromatics. the ring OR a lone pair in a p-orbital. Only one p The heteroatom can be a part of the conjugation as either part of a r bond orbital from the atom can align to contribute to the aromaticity. For example, let's look at furan (shown to the right). How many lone pairs are on the oxygen in this structure? O 3 lone pairs O 1 lone pair O 2 lone pairs O O lone pairs How many electrons are in the r bonds? O 0 electrons O 4 electrons O 2 electrons O 1 electron O 5 electrons O 3 electrons O 6 electrons To determine, the total number of x electrons to use for the Huckel calculation, you need to determine how many of the non-bonding electrons on the oxygen are aligned with the x bonds. Is the red orbital on oxygen aligned with r bonds? O yes O no Is the blue orbital on oxygen aligned with x bonds? O no O yes What is the total number of…arrow_forwardDetermine pro-R and pro-S?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning