1. Refer to the compounds below to answer the following questions: CO₂Et 0 C. H O O₂N-CH2-C-CH3 0 OEt || 111 A. Indicate all the acidic hydrogens in Compounds I through IV. IV B. Indicate which hydrogens in Compound II are the most acidic. Explain your answer C. Choose the most acidic compound from Compounds I - IV. Explain your choice.

1. Refer to the compounds below to answer the following questions: CO₂Et 0 C. H O O₂N-CH2-C-CH3 0 OEt || 111 A. Indicate all the acidic hydrogens in Compounds I through IV. IV B. Indicate which hydrogens in Compound II are the most acidic. Explain your answer C. Choose the most acidic compound from Compounds I - IV. Explain your choice.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter4: Acids And Bases

Section: Chapter Questions

Problem 4.33P: Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label...

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As 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.
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.
For 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).
Use Table 13-2 to order the following from the strongest to the weakest acid. HClO2,H2O,NH4+,HClO4
A very strong base can remove a proton from methylamine:
Rank the following compounds according to acidity, 1 being the most acidic and 4 being the least acidic. First, list the ranking number followed by the compound letter in order from 1 to 4, and then explain your reasoning in a sentence or two.
16. Select the most acidic compound from the series provided below. OH ОН CH₂OH H3C A -미 CN B pac CN COH CN
2. Which is the most acidic hydrogen in the following compound? Provide a brief explanation. H H H. H, II IV +H `H.
3. Rank the hydrogens in bold in the following molecules in order of their acidity. Rank the most acidic first down to the least acidic. I > ty > IV > 161 I H II H H III IV H
4. Label the three oxygens in compounds A, B, and C in order of Lewis basicity, with 1 being the most basic and 3 being the least. Explain your choice for the most basic one. B C H H H H F3C
Which is the stronger base, CH3PH or CH3S? Hint: Which base has the weaker conjugate acid? CH3-S: VS IA Η | ΠΙΑ LBe 11 12 Na Mg CH3-PH IIIA IVA VA VIA VILA He 9 10 B 68 80 104 106 106 107 108 100 110 Fr Ra Ac Ung Unp Unh Uns Uno Une Unn Select one: O A. CH3PH* O B. CH3S™ 51 13 Al 14 CNO F Ne Si 15 16 S "a P 37 38 30 40 41 42 43 44 45 46 47 48 40 50 Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te VIILA 66 57 56 72 73 74 75 76 77 78 791 80 81 82 83 Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi 22 23 24 25 26 27 28 29 30 31 32 -33 34 35 19 20 21 K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr 20 By By 30 E 17 CI Ar 18 61 62 63 54 I Xe 84 85 Po At Rn 86
4. Identify the second weakest acid and the third strongest acid out of the following compounds. HC1 CH4 NH3 PH3 H₂S