Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 19, Problem 19.16P
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The amount of tartaric acid is responsible for the tartness of wine and controls the acidity of the wine. Tartaric acid also plays a very significant role in the overall taste, feel and color of a wine. Tartaric acid is a diprotic organic acid The chemical formula for tartaric acid is C4H6O6 and its structural formula is HO2CCH(OH)CH(OH)CO2H.
A 50.00 mL sample of a white dinner wine required 21.48 mL of 0.03776 M NaOH to achieve a faint pink color. Express the acidity of the wine in terms of grams of tartaric acid, H2C4H4O6 (M. M. = 150.10) per 100 mL of wine. Assume that the two acidic hydrogens are titrated at the end point.
MM H2C4H4O6 = 150.10
MM NaOH = 40.00
Below is the balanced chemical equation for this titration.
Determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products:(a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.
Rank the Acidity of the following sets of compounds. Give an explanation for the answers.
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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- Carboxylic Acid Derivatives Resolve by synthesis, step by step.arrow_forwardWhich of the following compounds are acidic (A), basic (B), or relatively neutral (N). CH;-CH-S-H CH;-CH2-CH3 CH;-CH=CH2 CH;-CH,-0-CH, CH;-CH2-O-Harrow_forwardUsing the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.arrow_forward
- Complete the following acid-base reactions.arrow_forwardc201N Conpae Leaming. All Rights Roserved. Example 17.3 - Salts of Carboxylic Acids • Complete each acid-base reaction and name the carboxylic salt formed он COOH + NAOH (b) COOH + NaHCO,→ (a) (S)-Lactic acidarrow_forwardMethyllithium (CH3Li) is often used as a base in organic reactions. Predict the products of the following acid-base reaction.CH3CH2¬OH + CH3¬Li ¡arrow_forward
- The Keq for the reaction: A + B ↔ AB is 3.793 What is the Keq for 2 + AB ↔ 2 A + 2 B Keq = ?arrow_forwardNaHCO3 can deprotonate benzoic acid but cannot deprotonate phenol. On the other hand, NaOH can deprotonate both benzoic acid and phenol. Given this information, rank the molecules numbered I to V in order of decreasing acidity. COH cOH он H,0 H,CO, IV CH3 II I II (A) V > II >I > III > IV (В) II > 1 > V > III IV (C) II > V >I > IV > IIarrow_forwardPredict the position of equilibrium and calculate the equilibrium constant, Keq, for each acid-base reactionarrow_forward
- What is the conjugate acid of H2C6H7O5 -1aq2? What is its conjugate base?arrow_forwardAn unknown acid is chosen from the list in the 1223 Lab Procedure. Determine the Identify the unknown diprotic acid. The procedure for identifying an unknown acid is exactly as described in the lab manual. Part 1: Standardization of NaOH. 1.4378 g of oxalic acid was dissolved in 250.0 mL of water and a 25.00 mL aliquote was titrated with NaOH. 24.73 mL of titrant was required. Determine the concentration of sodium hydroxide. Answer: Part 2: Titration of the unknown acid. 1.9875 g of the unknown acid was dissolved in 250.0 ml of water and 25.00 ml of this solution was titrated with the NaOH. 29.50 mL of titrant was required. Determine the Molar Mass of the unknown. on Answer:arrow_forward3. For the following acid - base reaction, (a) predict the products; (b) identify the Bronsted acid, Bronsted base, conjugate acid, and conjugate base; (c) use curved arrows to show the flow of electron pairs in the reaction. CH3 CH2C-OH + NaNHaarrow_forward
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