Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 16.9C, Problem 16.17P
Show which of the nitrogen atoms in purine are basic, and which one is not basic. For the nonbasic nitrogen, explain why its nonbonding electrons ere not easily available to become protonated.
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need help with this along with an explanation on why it is most acidic ,etc?
please explain in detail with arrow pushing how you get to the answer,which hydrogen is most acidic and why?
Identify the most acidic compound between the following moleculesDraw the resonance structures of the conjugate base of the acid chosen in (a). Use the curved arrows to show the movement of electrons and the resonance arrows to show the relationship between these structures. All lone electron pairs and charges must be clearly indicated
Chapter 16 Solutions
Organic Chemistry (9th Edition)
Ch. 16.2 - Prob. 16.1PCh. 16.2 - Prob. 16.2PCh. 16.2 - a. Draw the resonance forms of benzene,...Ch. 16.2 - Show the product of the Diels-Alder dimerization...Ch. 16.4 - Prob. 16.5PCh. 16.6 - Make a model of cyclooctatetraene in the tub...Ch. 16.6 - Prob. 16.7PCh. 16.6 - Prob. 16.8PCh. 16.7 - Prob. 16.9PCh. 16.8A - a. Draw the molecular orbitals for the...
Ch. 16.8A - Repeat Problem16-10 for the cyclopentadienyl ions....Ch. 16.8C - Explain why each compound or ion should be...Ch. 16.8C - The following hydrocarbon has an unusually large...Ch. 16.8C - Prob. 16.14PCh. 16.8C - Prob. 16.15PCh. 16.9B - Prob. 16.16PCh. 16.9C - Show which of the nitrogen atoms in purine are...Ch. 16.9C - The proton NMR spectrum of 2-pyridone gives the...Ch. 16.9D - Prob. 16.19PCh. 16.9D - Prob. 16.20PCh. 16.10 - Prob. 16.21PCh. 16.12 - Ciprofloxacin is a member of the fluoroquinolone...Ch. 16.13 - Draw and name all the chlorinated benzenes having...Ch. 16.13 - Name the following compounds:Ch. 16.15 - The UV spectrum of 1-phenylprop-2-en-1-ol shows an...Ch. 16 - Prob. 16.26SPCh. 16 - Name the following compounds:Ch. 16 - Draw and name all the methyl, dimethyl, and...Ch. 16 - Four pairs of compounds are shown. In each pair,...Ch. 16 - One of the following hydrocarbons is much more...Ch. 16 - In Kekuls time cyclohexane was unknown, and there...Ch. 16 - Prob. 16.32SPCh. 16 - Azulene is a deep-blue hydrocarbon with resonance...Ch. 16 - Prob. 16.34SPCh. 16 - Prob. 16.35SPCh. 16 - Prob. 16.36SPCh. 16 - Prob. 16.37SPCh. 16 - Prob. 16.38SPCh. 16 - Prob. 16.39SPCh. 16 - Biphenyl has the following structure. a. Is...Ch. 16 - Anions of hydrocarbons are rare, and dianions of...Ch. 16 - How would you convert the following compounds to...Ch. 16 - Prob. 16.43SPCh. 16 - Prob. 16.44SPCh. 16 - A student found an old bottle labeled thymol on...Ch. 16 - Prob. 16.46SPCh. 16 - Prob. 16.47SPCh. 16 - Prob. 16.48SPCh. 16 - The proton NMR chemical shifts of the hydrogens in...Ch. 16 - Prob. 16.50SPCh. 16 - NMR has been used to probe many molecular...
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- The following are equivalent ways of asking about the acidity of an H atom: • What is the most acidic H on the molecule? • Which H is associated with the published pKa value? • Which H on the molecule is easiest to remove? • Which H on the molecule takes the least energy to remove? • Which bond to an H is most polarized? • For which H atom is removal least uphill in energy? • Which bond to an H atom, when broken, results in the lowest PE conjugate base? We will often find the last of these questions is easiest to answer. To do this, find all the different Hatoms on the molecule, and draw all possible conjugate bases.Only the lowest-energy one is the “real” conjugate base. Identify this structure, and you have found the most acidic H. Use this strategy to find the most acidic H on each of the following molecules. Note: Each structure hasat least three different kinds of H’s, so draw at least three unique conjugate bases for each.arrow_forwardComplete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. (a) (b) (c) (d)arrow_forwardSummarize the relationship between pKa and base strength by completing the followingsentences: a. For a given base, the higher the pKa of its conjugate acid, the stronger or weaker the base. b. For a given base, the lower the pKa of its conjugate acid, the stronger or weaker the base.arrow_forward
- Summarize the relationship between pKa and acid strength by completing the following sentences: a. The higher the pKa of an acid, the stronger or weaker the acid. b. The lower the pKa of an acid, the stronger or weaker the acid.arrow_forwardFor each molecule below, draw the conjugate acid or conjugate base or both if the molecule hasboth a conjugate acid and a conjugate base (e.g., water).arrow_forwardAs we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone.arrow_forward
- Complete each Lewis structure, draw all important resonance structures, predict a value for thebond angles requested, and explain your reasoning. a. Nitrous acid (HNO2)HONOHON=ONO= b. Enolate ion (C2H3O) HC1C2=HC2C1=arrow_forwardConsider the following bases: a. For each base above, circle the atom/atoms with the highest PE (will release the most P.E.when a lone pair on this atom combines with an H+ ) b. Rank the bases 1 (highest P.E./strongest base) to 7 (lowest PE/weakest base), and explainyour reasoning.arrow_forwardFor the previous four questions, label each molecule that appears in the question or your answer asstrong acid, strong base, weak acid, or weak base.arrow_forward
- Could you please explain in detail for example in figure B (yours)why the hydrogen next to O is not more acidic since Oxygen is more electronegative than carbon . In your D why the oxygen you chose is more basic than the other.please explain each choice .arrow_forwardChoose the stronger acid within the following pairs.arrow_forwardWhich of the following compounds is the stronger base? Explain. or NH3 is a v base than NCI3. This is due to the difference in the electron withdrawing strength of Cl compared with H. v is more electronegative than and will v more electron density v the nitrogen than Thus, the nitrogen atom in NCI3 has a v positive charge than it does in NH3. The v positive charge means that is v difficult to add H* to NCI3 than it is to add H* to NH3. Is the compound Sb(OH)5 likely to be acidic, basic, or neutral in water? Justify your answer. Phosphorus and arsenic form acids of the form X(OH)n, so one would predict that antimony would be similar as it is in the same family. Based in the number of OH groups present, it should be However, antimony hydroxides are not stable and form oxides which are known to be amphoteric. Thus, Sb(OH)6 is in fact more likely to bearrow_forward
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