Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 2, Problem 2.75P
Write a stepwise reaction sequence using proton transfer reactions to show how the
following reaction occurs. (Hint: As a first step, use
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Answer the following questions about acid-base equilibrium reactions.
(a)Which is a stronger acid HX or HY in the reaction below? HX + Y –→X –+ HYK eq= 2.43 x 10 –3
(b)What is the difference between a strong acid and a weak acid in terms of equilibrium position?
(c)If the Kaof H2CO3is 4.3 x 10 –7and the Kaof HF is 6.8 x 10 –4, then is the reaction below reactant favored or product favored?H2CO3+ F –→HCO3–+ HF
Write a stepwise reaction sequence using proton transfer reactions to show how the following reaction occurs. (Hint: As a first step, use −OH to remove a proton from the CH2 group between the C=O and C=C.)
Write a stepwise reaction sequence using proton transfer reactions toshow how the following reaction occurs. (Hint: As a first step, use −OH toremove a proton from the CH2 group between the C=O and C=C.)
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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- 8-15 Write an equation for the reaction that takes place when each base is added to water. (a) LiOH (b) (CH3)2NH (c) Sr(OH)2 (d) CH3CH2NH2arrow_forwardFormic acid, HCOOH, is found in ants. Write a balanced chemical equation to represent why an aqueous solution of formic acid is acidic.arrow_forwardIn each of the following acid-base reactions, identify the Brnsted acid and base on the left and their conjugate partners on the right. (a) C2H5N(aq) + CH3CO2H(aq) C5H5NH+(aq) + CH3CO2(aq) (b) N2H4(aq) + HSO4(aq) N2H5+(aq) + SO42(aq) (c) [Al(H2O)6]3+ (aq) + OH(aq) [Al(H2O)5OH]2+ (aq) + H2O+()arrow_forward
- Answer true or false to the following statements about the mechanism of acid-base reactions. (a) The acid and base must encounter each other by a collision in order for the proton to transfer. (b) All collisions between acids and bases result in proton transfer. (c) During an acid-base reaction the lone pair on the base fills the A-H antibonding sigma orbital.arrow_forwardBr what this reactan? products form as the result of OH BH3 2) H,02, NAOH.arrow_forwardComplete the equation for the following acid-base reaction. COOH OCH₂ Naegarrow_forward
- Identity the conjugation acid-base pairs in the following reactions. An acid donates a proton to become a conjugate base. A base accepts a proton to form a conjugate acid. 1.) HCO3 + NH3 → CO3² + NH4+ 2.) HCl + H₂O → H₂O* + CI 3.) CH3COOH + H₂O → H3O* + CH3COOarrow_forwardWhat is the reaction of the weak base C5H5N with water? O C5H5N + H2O → C5H5NH" + OH" O C5H5N + H20 → C5H5NH* + H3O* O C5H5N + H20 → C5H5NH* + OH¯ C5H5N + H20 → C5H4N° + H30+arrow_forwardAmmonia can react as an acid or a base. a) What is the conjugate acid of ammonia? b) What is the conjugate base of ammonia? c) arist dit ons servbed as Complete the following acid-base reaction in which NH3(e) acts as both an acid and a base: OcH 6 HOONH3() + NH3() = OOH (d FOZH (s *АНИ (1 sqz ions to biosqu adtaviðarrow_forward
- Consider the acid-base nature of the salt NH4[C6H5COO], when it is dissolved in water. (1) What are the acid-base properties of the cation, NH4+? (2) What are the acid-base properties of the anion, C6H5COO™? (3) Would an aqueous solution of NH4[C6H5COO] be acidic, basic or neutral? C ◊arrow_forwardFor the following chemical reaction, identify each rectant as an acid or base. Also, identify each product as a conjugate acid or base. NH3 + HCI ===== NH4+ + Cl-arrow_forwardWrite a stepwise reaction sequence using proton transfer reactions to show how the following reaction occurs. (Hint: As a first step, use OH to remove a proton from the CH2 group between the C=O and C=C.) + "OH H,0 (solvent)arrow_forward
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