Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 19, Problem 19.71P
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Draw the conjugate base and rank the compounds in order of increasing acidity. Explain the reason briefly
Rank the labeled protons (Ha–Hc) in mandelic acid, a naturally occurring carboxylic acid in plums and peaches, in order of increasing acidity. Explain in detail why you chose this order.
how do you arrange these compounds in terms of increasing acidity and match the Ka values to each compound,10,15,20. and what are the reasons for each choice.
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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- Br 2) Number these compounds in order of increasing acidity (most acidic = 1). COOH O₂N COOH COOH H₂C COOH COOHarrow_forwardRank 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.arrow_forwardWhich of the following compounds is a strongest base? NH₂ O₂N 01 Oll O III ON OV NH₂ = II E III NH₂ IV NH₂ NH₂arrow_forward
- The following questions are attached: a.arrow_forwardWhich compound, M or N, is the stronger acid? Explain your choice.arrow_forwardRank the labeled protons (Ha–Hc) in mandelic acid, a naturally occurring carboxylic acid in plums and peaches, in order of increasing acidity. Explain in detail why you chose this order.arrow_forward
- 2. Which base is stronger in each set? (a) H or CI (c) KCN or (b) NaOH or NaNHzarrow_forwardRank the following compounds in their correct order of acidity. 1=Most acidic and 4=least acidic.arrow_forwardRank the following compounds in order of increasing acidity, and explain in detail your choice of order.arrow_forward
- Which of the following compounds is the strongest base? O O O MeO 0₂N NH₂ -NH₂ NH₂ NH₂arrow_forwardPaylbenarrow_forward1. Arrange the substances by order of acidity or basicity as indicated. You may use pKa tables and periodic tables. H F, OH, NH2, CH3CH2CH2CH2 Weakest Base Weakest Acid CH3CH2OH, CH3COOH, HF, Benzene Strongest Base @ NH H NH₂ H NH₂ Weakest Acid Strongest Acid NH₂ Strongest Acidarrow_forward
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