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
Given the following partial structure, add a substituent X to C-1 so that it satisfies the indicated stereochemical requirement. What is the A -C - C - X torsion (dihedral) angle in each?
Zoapatanol is found in the leaves of Montanoa tomentosa, a flowering plant native to Mexico.
Classify the highlighted carbons in zoapatanol that are bonded to -OH groups as primary, secondary, tertiary, or quaternary
Which of the following projections would the most stable?
I believe that it would be the 6th because out of all 6 groups, the methyl groups are the furthest distance away from each other in the 6th. When they are in close proximity, the front and back methyl groups’ electron orbitals repel each other, which generates potential energy and makes the conformation unstable.
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
- Given the organic product form in each of the following reactions draw a 3-D representation for the product molecule showing its correct configuration. arrow_forwardWhat is the absolute stereochemistry at carbons 1,2,3, and 5 ?arrow_forwardThe most stable conformation of most aldopyranoses is one in which the largest group, the CH2OH group, is equatorial. However, alpha-D-idopyranose exists primarily in a conformation with an axial CH2OH group. Write formulas for the two chair conformations of a-D-idopyranose (one with the CH2OH group axial and one with the CH2OH group equatorial) and provide an explanationarrow_forward
- In RPLC, Compound A is more polar than compound B. In which column will compound A be more retained than compound B? A. C18 B. C8 C. Phenyl bounded column D. All of the above E. None of the abovearrow_forwardWhich is the most stable projection of 2-methylbutane?arrow_forwardFor the 6-carbon molecule below, how would you expect it to break into two pieces? a. two 3-carbon units b. one 2-carbon unit and one 4-carbon unit c. one 1-carbon unit, one 2-carbon unit, and one 3-carbon unit d. one 1-carbon unit and one 5-carbon unit I'm having a hard time identifying the correct location of Beta and Alpha. If the carbonyl beta is the second bond over from carbonyl, then the breakage would occur at bond C3-C4. This would then result in two 3-carbon units, right? The molecule in the image looks like fructose which would result in two 3-carbon units.arrow_forward
- Which of the following substituents are meta directing in electrophilic aromatic substitution? A. CO2H, NO2, CF3 B. OEt, COCH3, Br C. NH2, Me, CCl3 D. F, CF3, OC(O)CH3arrow_forwardWhich of the following is FALSE regarding terminal alkynes? The proton in the terminal carbon is weakly acidic. They react with H₂O, H₂SO4, HgSO4 to produce an aldehyde. The hydrohalogenation reaction yields a geminal dihalide. Treatment with alcoholic AgNO3 produces a silver acetylide.arrow_forwardIdentify the correct prochiral hydrogen which has been replaced by Br in the ketone shown below.arrow_forward
- How many hydrogens are implied at the indicated carbons?arrow_forwardCitrate synthase, one of the enzymes in the series of enzyme-catalyzed reactions known as the citric acid cycle, catalyzes the synthesis of citric acid from oxaloacetic acid and acetyl-CoA. If the synthesis is carried out with acetyl-CoA that contains radioactive carbon (14C) in the indicated position , the isomer shown here is obtained. a. Which stereoisomer of citric acid is synthesized: R or S? b. If the acetyl-CoA used in the synthesis contains 12C instead of 14C, will the product of the reaction be chiral or achiral?arrow_forwardWhat are the degrees of unsaturation in the following molecule?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