ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 25, Problem 25.42P
Decide which
a. b.
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Decide which N atom in each molecule is most basic and draw the product formed when each compound is treated with CH3CO2H. Zolpidem (trade name Ambien) is used to treat insomnia, whereas aripiprazole (trade name Abilify) is used to treat depression, schizophrenia, and bipolar disorders.
Answer the following questions about esmolol, a drug used to treat high blood pressure sold under the trade name Brevibloc.a.Label the most acidic hydrogen atom in esmolol.
b.What products are formed when esmolol is treated with NaH?
c.What products are formed when esmolol is treated with HCl?
d. Label all sp2 hybridized C atoms.
e.Label the only trigonal pyramidal atom.
f.Label all C's that bear a δ+ charge.
Answer the following questions about esmolol, a drug used to treat high blood pressure sold under the trade name Brevibloc.a.Label the most acidic hydrogen atom in esmolol.
b.What products are formed when esmolol is treated with NaH?
c. What products are formed when esmolol is treated with HCl?
d.Label all sp2 hybridized C atoms.
e. Label the only trigonal pyramidal atom.
f. Label all C's that bear a δ+ charge.
Chapter 25 Solutions
ORGANIC CHEMISTRY
Ch. 25 - Prob. 25.1PCh. 25 - Prob. 25.2PCh. 25 - Prob. 25.3PCh. 25 - Prob. 25.4PCh. 25 - Prob. 25.5PCh. 25 - Prob. 25.6PCh. 25 - Problem 25.7
Draw the product of each...Ch. 25 - Prob. 25.8PCh. 25 - Prob. 25.9PCh. 25 - Prob. 25.10P
Ch. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Problem 25.18
Write out steps to show how each of...Ch. 25 - Prob. 25.19PCh. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Problem 25.22
Which nitrogen atom in each compound...Ch. 25 - Prob. 25.23PCh. 25 - Prob. 25.24PCh. 25 - Prob. 25.25PCh. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Problem 25.28
Draw the major product formed in...Ch. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Problem 25.31
Devise a synthesis of each compound...Ch. 25 - Prob. 25.32PCh. 25 - Problem 25.33
What starting materials are needed...Ch. 25 - Problem 25.34
(a) What two components are needed...Ch. 25 - Prob. 25.35PCh. 25 - Prob. 25.36PCh. 25 - 25.37 Varenicline (trade name Chantix) is a drug...Ch. 25 - Give a systematic or common name for each...Ch. 25 - Prob. 25.39PCh. 25 - 25.40 How many stereogenic centers are present in...Ch. 25 - 25.41 Rank the compounds in each group in order of...Ch. 25 - 25.42 Decide which atom in each molecule is most...Ch. 25 - 25.43 Explain why pyrimidine is less basic than...Ch. 25 - 25.44 Rank the nitrogen atoms in each compound in...Ch. 25 - 25.45 Explain why nitroaniline is a stronger base...Ch. 25 - 25.46 Explain the observed difference in the...Ch. 25 - 25.47 Why is pyrrole more acidic than...Ch. 25 - Prob. 25.48PCh. 25 - Prob. 25.49PCh. 25 - Prob. 25.50PCh. 25 - 25.51 How would you separate toluene , benzoic...Ch. 25 - 25.52 Draw the products formed when methylaniline ...Ch. 25 - Prob. 25.53PCh. 25 - Prob. 25.54PCh. 25 - 25.55 Draw the organic products formed in each...Ch. 25 - Prob. 25.56PCh. 25 - 25.57 Identify A, B, and C, three intermediates in...Ch. 25 - Prob. 25.58PCh. 25 - Prob. 25.59PCh. 25 - 25.60 A chiral amine A having the configuration...Ch. 25 - 25.61 Draw a stepwise mechanism for each...Ch. 25 - 25.62 Draw a stepwise mechanism for the following...Ch. 25 - Prob. 25.63PCh. 25 - 25.64 Tertiary aromatic amines react with and ...Ch. 25 - 25.65 Devise a synthesis of each compound from...Ch. 25 - Prob. 25.66PCh. 25 - Prob. 25.67PCh. 25 - Prob. 25.68PCh. 25 - Prob. 25.69PCh. 25 - 25.70 Devise a synthesis of each biologically...Ch. 25 - 25.71 Devise a synthesis of each compound from...Ch. 25 - 25.72 Three isomeric compounds A, B, and C, all...Ch. 25 - 25.73 Treatment of compound D with LiAlH4 followed...Ch. 25 - Prob. 25.74PCh. 25 - 25.75 Rank the following compounds in order of...Ch. 25 - Prob. 25.76PCh. 25 - Prob. 25.77PCh. 25 - Prob. 25.78P
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- Decide which N atom in each molecule is most basic and draw the product formed when each compound is treated with CH;CO,H. Benazepril (trade name Lotensin) is a ß blocker used to treat high blood pressure and congestive heart failure. Abilify is the trade name for aripiprazole, a drug used to treat depression, schizophrenia, and bipolar disorders. a. NH b. NH aripiprazole ČH,CO2H benazeprilarrow_forwardRank the attached ions in order of increasing basicity.arrow_forwardDraw the products of each acid–base reaction.arrow_forward
- What product is formed when each compound is treated with NaH? Each of these acid–base reactions was a step in a synthesis of a commercially available drug.arrow_forwardRank the labeled N atoms in the anticancer drug imatinib (trade name Gleevec) in order of increasing basicity. Imatinib, sold as a salt with methanesulfonic acid (CH3SO3H), is used for the treatment of chronic myeloid leukemia as well as certain gastrointestinal tumors.arrow_forwardRank the nitrogen atoms in each compound in order of increasing basicity. Isoniazid is a drug used to treat tuberculosis, whereas histamine (Section 25.6B) causes the runny nose and watery eyes associated with allergies. NH2 NHNH2 b. а. isoniazid histaminearrow_forward
- The 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_forwardNot sure if B would be the right onearrow_forward8arrow_forward
- Rank the compounds in each group in order of increasing basicity.arrow_forwardRank the nitrogen atoms in each compound in order of increasing basicity. Isoniazid is a drug used to treat tuberculosis, whereas histamine (Section 25.6B) causes the runny nose and watery eyes associated with allergies.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_forward
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