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ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 19, Problem 19.37P
Which compound in each pair has the lower
a. or
b. or
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16.43 Draw the products of each reaction.
a.
b.
d.
HO
C.
H
Lore
L
sob
Br₂
FeBr3
e.
NO₂
Br
HNO3
H₂SO4
CI
AICI 3
Cl₂
FeCl3
SO3
H₂SO4
Explain why HCl reacts more rapidly with compound A than compound B.
A
H
H₂C
H
CH
H
B
16.34 For which compounds can a second resonance structure be drawn? Draw an additional resonance structure for each
resonance-stabilized compound.
a.
OCH₂
b.
OCH₂
C.
d.
NHCH,
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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- 16.41 Draw the products of each reaction. a. b. HO NO₂ mellanrios H HNO3 H₂SO4 Br₂ FeBr3 AICI3 d. e. Br- edmun adtonie F prier f. F (X) napoln NO₂ Cl₂ FeCl3 SO3 H₂SO4 onho sur + Na Sarrow_forwardWhich compound in each pair is the stronger acid? a. or b. orarrow_forwardThe boiling points of a range of organic compounds (A-D) of similar Mol. Wt.s are given below. OH OMe A в D b.p. 46-50°C Explain why the boiling point of C is higher than that of D. Explain why the boiling point of B is higher than that of A. Explain why the boiling point of C is higher than that of A. Which of these four compounds is most acidic? What makes it so acidic? b.p. 78'C b.p. 141'C b.p. 79'C (i) (ii) (iii) (iv)arrow_forward
- Two other commonly used sulfonic acids are methanesulfonic acid (CH3SO3H) and triuoromethanesulfonic acid (CH3SO3H). Which has the weaker conjugate base? Which conjugate base is the better leaving group? Which of these acids has the higher pKa?arrow_forward1. Which is more acidic in each pair of compounds? a. CH3CH2OH vs CF3CH2OH b. Methanol vs 2-propanol c. CH3CF2OH vs CH3CCI2OH d. CH3CHFOH vs CH2FCH2OHarrow_forwardWhich compound in each pair is the stronger acid? c. CH3COOH or O,NCH,COOH a. CICH,COOH or FCH,COOH b. Cl,CHCH,OH or Cl,CHCH,CH,OHarrow_forward
- How does the reaction shown effect the water solubilty of the product? H HCI dhe A. product is more water soluble than the parent compound B. product is less water soluble than the parent compoundarrow_forward12) Which compound is stronger base? a) b) D A d) all the samearrow_forwardTwo other commonly used sulfonic acids are methanesulfonic acid (CH3SO3H) and trifluoromethanesulfonic acid (CH3SO3H). Which has the weaker conjugate base? Which conjugate base is the better leaving group? Which of these acids has the higher pKa?arrow_forward
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