Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 2, Problem 2.53P
The
a. For each compound, draw the conjugate base, including all possible resonance structures.
b. Explain the observed trend in
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Part IV: ARIO
1. Why is H-Cl a stronger acid than H-F but CCI,COOH is weaker acid than CF3COOH? Make sure to
explain your answer using ARIO.
2. Rank the following bases in decreasing order of their Ka values
N
A
A
H
N
B
B
HIN
3. Which of the following highlighted hydrogens is easiest to donate?
C
с
NH₂
D
D
For the following acid-base reaction, predict the position of the equilibrium and identify the most stable base.
+
NaOH
||
A. favor the right side with compound I being the most stable base
B. favor the right side with compound II being the most stable base
OC. favor the right side with compound III being the most stable base
OD. favor the left side with compound I being the most stable base
E. favor the left side with compound II being the most stable base
سمیر
|||
+
H₂O
IV
6. Which of the following compounds has the lowest pKa ?
A
OH
NH
B
XOH
OH
C
X
D
NH₂
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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- 5. sy For each reaction, identify the acid, base, conjugate acid, and conjugate base. Determine which direction the reaction will favor. Ka H₂SO3 = 1.54 x 10-2 and 1.07 x 10-7 Kb of CH3NH₂ = 4.4 x 10-4 Ka of CH3OH = 3.20 x 10-16 a. CH3O+ NH3 CH3OH + NH₂ b. HSO3 + CH3NH2 H₂SO3 + CH3NH3* c. 2HF + Ca(OH)2 2H₂O + CaF2arrow_forwardFor the following reaction: OH NH a-Label the acid and base in the starting materials. b-Draw the conjugate acid and conjugate base. c-Label the conjugate acid and conjugate base. d-Give the approximate pka of the acid and conjugate acid. e-State whether the reaction will proceed more toward reactants or toward products.arrow_forwardIn each row of the table, select the stronger base. N. CH3 N. CI t N.arrow_forward
- What is the CORRECT product A for the following reaction? i. Mg, Et,O ii. CO2 iii. H;O* i. LİAH, Et,O ii. H2O Br Aarrow_forwardUse the information in the pK table to rank the molecules in order of decreasing basicity. For example, select "1" in the second column for the strongest base a and "2" for the next strongest base and so on. CH3 HS F CH,CO, Molecules (Choose one) (Choose one) (Choose one) (Choose one) X Ś CHA 4 NH₂ H₂ CH3NH₂ 2 48 38 36 33 pk table pKa CH,NH, CH₂SH 10.4 H₂O* HCN + 10.6 9.4 NH H₂O 15.7 H₂S CH₂OH 15.5 CH,CO,H 4.76 9.2 7.00 HF CH₂OH₂ H₂SO4 HC1 HBr 3.17 -1.7 -2.2 -3.0 -7 -9arrow_forwardFor each of the pairs shown, decide which is the strongest base. O,N O,N- A O,N- A NH NH2 A B 1. A is the strongest base 2. B is the strongest base 3. The bases have approximately equal strength > > >arrow_forward
- 1. What is the structure of N,N-diethylaniline? CH₂CH3 CH3 B 2. Which of the following compounds is least soluble in water? NH₂ A O₂N A. IB. II C. III D. both I and III 3. Which of the following compounds is the strongest base? NH₂2 NH₂ NH₂ III NH₂ A. I B. II C. III D. IV E. V IV NH₂ с NH₂arrow_forwardConsider two acids: C,H5CO,H (benzoic acid, pK = 4.2) and HCO,H (formic acid, pK=3.8). Which acid is the stronger acid? Select the single best answer. formic acid benzoic acidarrow_forwardWhat does a value of K eq greater than 1 mean?A. More reactants than products exist at equilibrium.B. More products than reactants exist at equilibrium.C. The rate of the forward reaction is high atequilibrium.D. The rate of the reverse reaction is high atequilibrium.arrow_forward
- hydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone. CH,ČCH, H CH,CH, H Acetone Ethane pK, 20.2 pK, 51arrow_forward4. Circle the stronger acid between each pair of compounds. Give the factor that would cause this. Draw the stronger conjugate b. base of the two. a. CF3CH₂OH A OH B A LOH B LOH Draw the stronger conjugate base of the two.arrow_forward1. Consider the generic acids: HX, HY, and HZ. Which is the strongest acid? 60 HX OHt OX- HZ HZ OH OZ- HY HY OH OY-arrow_forward
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