Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 2, Problem 2.71P
DBU,
reaction in chapter 8, Which N atom is more basic in DBU? Explain your choice.
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11) For the following reaction, identify the Lewis acid and the Lewis base and draw the curved
arrow mechanism.
H H
-N -
+)
NH2
lewis
base
lewis Aciol
SHN pinb!7 (P
12) Which of the following solvents can be used with NaNH2 and why?
02H (2
(9
HOʻHO H
A.
Rank the following compounds in order of increasing acidity (1 = least acidic, 3 = most acidic) and in the space provided use resonance (of the conjugate base) to explain why the compound you have labelled “3” is the most acidic.
2)
-OH
phenylacetic acid
K₂ = 5.2 x10-5
+
propionic acid pK, = 4.87
Using the information above, draw the products of the reaction and determine if the reaction is
reactant- or product-favored. Briefly elaborate on how the equilibrium was determined.
H3C
H3C
OH
OH
Chapter 2 Solutions
Organic Chemistry
Ch. 2 - a. Which compounds are Bronsted-Lowry acids:...Ch. 2 - a. Draw the conjugate acid of each base:...Ch. 2 - Label the acid and base, and the conjugate acid...Ch. 2 - Draw the products of each proton transfer...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Which compound in each pair is the stronger acid?...Ch. 2 - Use a calculator when necessary to answer the...Ch. 2 - Rank the conjugate bases of each of group of acids...Ch. 2 - Problem-2.10 Considers two acids: (formic acid,)...Ch. 2 - Estimate the pKa of each of the indicated bonds.
Ch. 2 - Draw the products of each reaction and determine...Ch. 2 - Prob. 2.12PCh. 2 - Without reference to a pKa table, decide which...Ch. 2 - which compound in each pair of isomers is the...Ch. 2 - Prob. 2.15PCh. 2 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2 - whichcompound in each pair is the stronger acid? a...Ch. 2 - Glycolic acid, HOCH2CO2H, is the simplest member...Ch. 2 - Explain the apparent paradox. HBr is a stronger...Ch. 2 - The CH bond in acetone, (CH3)2C=O, has a pKa of...Ch. 2 - Acetonitrile (CH3CN) has a pKa of 25, making it...Ch. 2 - For each pair of compounds: [1] Which indicated H...Ch. 2 - Rank the compounds in each group in order of...Ch. 2 - Which proton in each of the following drugs is...Ch. 2 - Prob. 2.25PCh. 2 - Problem 2.29
Compounds like amphetamine that...Ch. 2 - Problem 2.30 Which species are Lewis bases?
a. b....Ch. 2 - Which species are Lewis acids?
a. b. c. d.
Ch. 2 - For each reaction, label the Lewis acid and base....Ch. 2 - Prob. 2.30PCh. 2 - Prob. 2.31PCh. 2 - Prob. 2.32PCh. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - Prob. 2.35PCh. 2 - Prob. 2.36PCh. 2 - a Draw the conjugate acid of ethylene, CH2 = CH2....Ch. 2 - 2.40 Draw the products formed from the acid-base...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Prob. 2.40PCh. 2 - Draw the product of acid-base reaction. a. c. b....Ch. 2 - Prob. 2.42PCh. 2 - Prob. 2.43PCh. 2 - What is Ka for each compound? Use a calculator...Ch. 2 - What is the pKa for each compound? a. b. c.Ch. 2 - Which of the following bases are strong enough to...Ch. 2 - Which compounds can be deprotonated by OH, so that...Ch. 2 - Draw the product of each reaction. Use the pKa...Ch. 2 - Rank the following compounds in order of...Ch. 2 - Rank the following ions in order of increasing...Ch. 2 - Prob. 2.51PCh. 2 - Prob. 2.52PCh. 2 - The pKa of three CH bonds is given below. a. For...Ch. 2 - a. What is the conjugate acid of A? b. What is the...Ch. 2 - 2.56 Draw the structure of a constitutional isomer...Ch. 2 - 2.57 Many drugs are Bronsted-Lowry acids or...Ch. 2 - Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH)...Ch. 2 - Prob. 2.58PCh. 2 - Ethyl butanoate, CH3CH2CH2CO2CH2CH3, is one of the...Ch. 2 - Prob. 2.60PCh. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 2.62PCh. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Prob. 2.64PCh. 2 - Draw the products of each Lewis acid-base...Ch. 2 - Prob. 2.66PCh. 2 - Prob. 2.67PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - Prob. 2.70PCh. 2 - 2.72 DBU, is a base we will encounter in...Ch. 2 - 2.73 Molecules like acetamide can be protonated...Ch. 2 - Two pKa values are reported for malonic acid, a...Ch. 2 - Prob. 2.74PCh. 2 - 2.76 Write a stepwise reaction sequence using...Ch. 2 - Prob. 2.76PCh. 2 - 2.78 Which compound, M or N, is the stronger acid?...
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- 4&6 are attached questions, thank you!arrow_forward4. The following two compounds are protonated when treated with one mole equivalent of a strong acid (e.g. HCI). For each compound, draw the equilibrium to show the preferred site of protonation and give an estimate of the base strength (pKaH). -OHarrow_forward11.arrow_forward
- (10) Rank the following compounds from most to least acidic. 2 NH2 Y OHarrow_forward4. The pk, of vanillin is about 9, which is much more acidic than a normal alcohol. Draw a reaction showing the deprotonation of vanillin with NaOH, and then draw six resonance structures of the conjugate base. Draw the hybrid structure and clearly indicate how the negative charge is distributed in the compound.arrow_forward8. (8) Circle the most acidic compound from each set below. Then, list the structural influence(s) that best explains your answer. structural influences: Resonance, atom size, electronegativity, hybridization, and inductive effect. CI HO. NH2 HO A) B)arrow_forward
- NO2 would stabilize an adjacent (-) charge through resonance, making it a –R substituent What is the more acidic proton in nitrocyclohexane? explain with proper resonance structures of the conjugate base.arrow_forwardPhenol (hydroxybenzene) behaves as a weak acid. a) Write out the equilibrium equation for its partial dissociation in water. b) Write out the expression for the acid dissociation constant, Ka. d) Draw the conjugate base of phenol and show how it is stabilised by resonance. e) Compare and explain the acidity of phenol (p = 9.9) with that of: cyclohexanol (pk = 16.0) 3-fluorophenol (pK₁ = 9.3) 4-acetylphenol (pK, = 8.1)arrow_forward9:48 Aa 9:44 AM, Apr 22 Save Share II Give the arrow pushing meehanium for the following reaetion LBA acctonearrow_forward
- Select the stronger base and then draw its conjugate acid below. CICH₂CH₂O or CH3CH₂O- • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • You do not have to include lone pairs in your answer. Ⓡ OO. n[1] ? ChemDoodlearrow_forwardMm.44.arrow_forward7. a) Write "most" under the compound which is most reactive toward C/FeClg. Write "least" under the compound which is least reactive toward Cl/FeClg. H-N NO2 b) Write "most" under the compound which is most acidic. Write "least" under the compound which is least acidic. OH OH N. c) Write "highest" under the underlined carbon in the highest oxidation state. Write "lowest" under the underlined carbon in the lowest oxidation state. HCOCH3 CH;CH3 CH:OH H2C=Oarrow_forward
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