Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 19, Problem 19.15P
Rank the labeled protons
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2-Hydroxybutanedioic acid occurs naturally in apples and other fruits. Rank the labeled protons in 2-hydroxybutanedioic acid in order of increasing acidity.
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Chapter 19 Solutions
Organic Chemistry
Ch. 19 - Prob. 19.1PCh. 19 - Problem 19.2 Give the structure corresponding to...Ch. 19 - Problem 19.3 Draw the structure corresponding to...Ch. 19 - Prob. 19.4PCh. 19 - Prob. 19.5PCh. 19 - Problem 19.6 Rank the following compounds in order...Ch. 19 - Problem 19.7 Explain how you could use IR...Ch. 19 - Prob. 19.8PCh. 19 - Problem 19.9 How many tetrahedral stereogenic...Ch. 19 - Problem 19.10 What alcohol can be oxidized to each...
Ch. 19 - Problem 19.11 Identify A-D in the following...Ch. 19 - Problem 9.12 Draw the cation that results when a...Ch. 19 - Problem 19.13 Draw the products of each acid-base...Ch. 19 - Problem 19.14 Given the values in Appendix A,...Ch. 19 - Problem 19.15 Rank the labeled protons in...Ch. 19 - Problem 19.16 Match each of the following values ...Ch. 19 - Problem 19.17 Rank the compounds in each group in...Ch. 19 - Problem 19.18 Rank the compounds in each group in...Ch. 19 - Prob. 19.19PCh. 19 - Problem 19.20 Which of the following pairs of...Ch. 19 - Problem 19.21 Two other commonly used sulfonic...Ch. 19 - Problem 19.22 Draw both enantiomers of each amino...Ch. 19 - Problem 19.23 Explain why amino acids, unlike most...Ch. 19 - Problem 19.24 Draw the positively charged,...Ch. 19 - Prob. 19.25PCh. 19 - Problem 19.26 Explain why the of the group of...Ch. 19 - Answer each question for A and B depicted in the...Ch. 19 - Prob. 19.28PCh. 19 - 19.29 Give the IUPAC name for each compound.
a....Ch. 19 - 19.30 Draw the structure corresponding to each...Ch. 19 - Prob. 19.31PCh. 19 - 19.32 Rank the following compounds in order of...Ch. 19 - 19.33 Draw the organic products formed in each...Ch. 19 - 19.34 Identify the lettered compounds in each...Ch. 19 - 19.35 Using the table in Appendix A, determine...Ch. 19 - 19.36 Draw the products of each acid-base...Ch. 19 - 19.37 Which compound in each pair has the lower ?...Ch. 19 - 19.38 Rank the compounds in each group in order of...Ch. 19 - 19.39 Rank the compounds in each group in order of...Ch. 19 - 19.40 Match the values to the appropriate...Ch. 19 - Prob. 19.41PCh. 19 - 19.42 Which carboxylic acid has the lower ,...Ch. 19 - Prob. 19.43PCh. 19 - 19.44 Explain the following statement. Although...Ch. 19 - Prob. 19.45PCh. 19 - 19.46 Explain why the of compound A is lower than...Ch. 19 - 19.47 Rank the following compounds in order of...Ch. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - 19.50 Draw all resonance structures of the...Ch. 19 - As we will see in Chapter 23, CH bonds are...Ch. 19 - Prob. 19.52PCh. 19 - The pKa of acetamide (CH3CONH2) is 16. Draw the...Ch. 19 - 19.54 Write out the steps needed to separate...Ch. 19 - Prob. 19.55PCh. 19 - Can octane and octan -1- ol be separated using an...Ch. 19 - 19.57 Identify each compound from its spectral...Ch. 19 - 19.58 Use the NMR and IR spectra given below to...Ch. 19 - 19.59 An unknown compound (molecular formula )...Ch. 19 - 19.60 Propose a structure for (molecular formula...Ch. 19 - 19.61 Match the data to the appropriate...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.64PCh. 19 - 19.65 For each amino acid ,draw its neutral,...Ch. 19 - Calculate the isoelectric point for each amino...Ch. 19 - 19.67 Lysine and tryptophan are two amino acids...Ch. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - Prob. 19.70PCh. 19 - 19.71 Hydroxy butanedioic acid occurs naturally in...Ch. 19 - 19.72 Although it was initially sold as a rat...
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- Answer true or false to the following statements about the mechanism of acid-base reactions. (a) The acid and base must encounter each other by a collision in order for the proton to transfer. (b) All collisions between acids and bases result in proton transfer. (c) During an acid-base reaction the lone pair on the base fills the A-H antibonding sigma orbital.arrow_forwardRank the following substances in order of increasing acidity: (a) (CH3)2CHOH, HC≡CH, (CF3)2CHOH, CH3OH (b) Phenol, p-methylphenol, p-[trifluoromethyl) phenol (c) Benzyl alcohol, phenol, p-hydroxybenzonic acidarrow_forwardWhich has the larger numerical value? (a) The pKa of a strong acid or the pKa of a weak acid (b) The Ka of a strong acid or the Ka of a weak acidarrow_forward
- A very strong base can remove a proton from methylamine:arrow_forwardArrange the following compounds in order of decreasing acidity. I || > ||| > | O III >> || ||| > || > | O I > I| > ||| CH₂ II III 0arrow_forwardWhich base, CH3NH2 or (CH3)2NH, is the stronger base? Which conjugate acid, (CH3)2 NH2+ or(CH3)2 NH3+ , is the stronger acid?arrow_forward
- Draw the structure for the conjugate acid of the base shown. Be sure to include all lone pairs and formal charges (if applicable) on the structure. H Harrow_forwardWhich 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 86arrow_forwardIn each row of the table, select the stronger base. HO NH to alo CH3 N_ CI N_ OHarrow_forward
- Choose the strongest base. Digion OH3C-NH₂ NH₂ NH₂ NO₂ NH₂arrow_forwardConsider the two following nitrophenol structures: OH OH `NO2 NO2 p-nitrophenol m-nitrophenol Predict which will be the stronger acid. (Hint: Consider possible resonance structures analogous to those given in the text for phenol.)arrow_forward
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