ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 2, Problem 2.54P
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
Please don't provide handwriting solution
For each compound, indicate the atom that is most apt to be protonated
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 each statement as True or False.
a. is the...Ch. 2 - Label the acid and base, and the conjugate acid...Ch. 2 - Decide which compound is the acid and which is the...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 - Prob. 2.11PCh. 2 - Draw the products of each reaction and determine...Ch. 2 - Prob. 2.13PCh. 2 - Without reference to a pKa table, decide which...Ch. 2 - Rank the labeled H atoms in the following compound...Ch. 2 - Which hydrogen in each molecule is most...Ch. 2 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2 - Which compound in each pair of isomers is the...Ch. 2 - Which compound in each pair is the stronger acid?...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 - Which anion A or B is the stronger base? ABCh. 2 - Prob. 2.28PCh. 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. 2.33PCh. 2 - Prob. 2.34PCh. 2 - Label the Lewis acid and base. Use curved arrow...Ch. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - 2.38 What is the conjugate acid of each base?
a....Ch. 2 - 2.39 What is the conjugate base of each acid?
a....Ch. 2 - 2.40 Draw the products formed from the acid-base...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Draw the products of each proton transfer...Ch. 2 - Prob. 2.43PCh. 2 - Prob. 2.44PCh. 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 products of each reaction. Use the pKa...Ch. 2 - Rank the following compounds in order of...Ch. 2 - 2.51 Rank the following ions in order of...Ch. 2 - Prob. 2.52PCh. 2 - Prob. 2.53PCh. 2 - 2.54 The of three 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 - 2.59 Atenolol is a (beta) blocker, a drug used to...Ch. 2 - 2.60 Use the principles in Section 2.5 to label...Ch. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 2.62PCh. 2 - 2.63 Classify each compound as a Lewis base, a...Ch. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Label the Lewis acid and Lewis base in each...Ch. 2 - 2.66 Draw the products of each Lewis acid-base...Ch. 2 - Prob. 2.67PCh. 2 - 2.68 Answer the following questions about the four...Ch. 2 - Prob. 2.69PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - 2.72 DBU, is a base we will encounter in...Ch. 2 - 2.73 Molecules like acetamide can be protonated...Ch. 2 - Prob. 2.74PCh. 2 - Prob. 2.75PCh. 2 - 2.76 Write a stepwise reaction sequence using...Ch. 2 - Prob. 2.77PCh. 2 - 2.78 Which compound, M or N, is the stronger acid?...
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- 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 IVarrow_forward6. Which of the following compounds has the lowest pKa ? A OH NH B XOH OH C X D NH₂arrow_forward5. 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_forward
- In each row of the table, select the stronger base. N. CH3 N. CI t N.arrow_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_forwardFor the following molecules, identify the acidic hydrogens from among those that are bolded. For each acidic hydrogen that you identify, draw the conjugate base that results from a base removing that acidic hydrogen. For molecules with more than one acidic hydrogen, draw a separate conjugate base for each one.arrow_forward
- Use 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_forwardBb.65.arrow_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_forward
- Which is a stronger base?arrow_forwardPredict the of the acid-base equilibrium. Be sure to be able to explain why. LOH он + Starting materials (SMs) favoured 50:50 distributions of SMs and products Products favoured Need more information to be able to decidearrow_forward1. 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_forward
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