Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 5, Problem 10E
Phenol (shown below) has a
a. Based on
b. Draw the conjugate base of phenol (called phenoxide) including allimportant resonance structures.
c. Construct an explanation for why phenol is a stronger acid than anordinary alcohol. (You may want to consider first why phenoxide is lowerin PE than methoxide
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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
IV
Which is the more stable base? a. Br− or I− b. CH3O− or CH3S− c. CH3CH2O− or CH3COO− d. H2C CH or HC C− e. FCH2CH2COO− or CH2CH2COO- f. CLCH2CH2O- or CL2CHCH2O-
In each reaction, Label the reactants as a Lewis base (nucleophile) or a Lewis acid
(electrophile). Use curved arrows to show the movement of electron pairs in the reaction.
NH,
H-C-
H-
H.
ONH3
Chapter 5 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 5 - Which elements on the periodic table (other than...Ch. 5 - You will not find “hydroxide” in the stockroom,...Ch. 5 - Prob. 3CTQCh. 5 - Prob. 4CTQCh. 5 - Prob. 5CTQCh. 5 - Prob. 6CTQCh. 5 - On which do you expect to have a more intense and...Ch. 5 - Prob. 8CTQCh. 5 - Prob. 9CTQCh. 5 - Prob. 10CTQ
Ch. 5 - Prob. 11CTQCh. 5 - Prob. 12CTQCh. 5 - Prob. 13CTQCh. 5 - Prob. 14CTQCh. 5 - Prob. 15CTQCh. 5 - Prob. 16CTQCh. 5 - For each proposed set of resonance structures: a....Ch. 5 - Consider the polarization of the C=O bond in the...Ch. 5 - The C=O double bond is called a “carbonyl bond.”...Ch. 5 - Prob. 20CTQCh. 5 - Prob. 21CTQCh. 5 - Prob. 22CTQCh. 5 - Prob. 23CTQCh. 5 - Prob. 24CTQCh. 5 - Prob. 25CTQCh. 5 - Prob. 26CTQCh. 5 - Prob. 27CTQCh. 5 - Prob. 28CTQCh. 5 - Prob. 29CTQCh. 5 - Prob. 30CTQCh. 5 - Prob. 31CTQCh. 5 - Confirm that there is no legitimate Lewis...Ch. 5 - Draw all resonance structures of the molecule...Ch. 5 - Prob. 34CTQCh. 5 - Prob. 35CTQCh. 5 - Prob. 36CTQCh. 5 - Occasionally, we will see an ionic compound that...Ch. 5 - Prob. 2ECh. 5 - Prob. 3ECh. 5 - Prob. 4ECh. 5 - Is it possible to draw a resonance structure of...Ch. 5 - Prob. 6ECh. 5 - Prob. 7ECh. 5 - Prob. 8ECh. 5 - Phenol (shown below) has a pKa10 . a. Based on pKa...Ch. 5 - Use curved arrows to show the most likely...Ch. 5 - Prob. 12ECh. 5 - Complete each Lewis structure, draw all important...Ch. 5 - Use curved arrows to show the most likely...Ch. 5 - Construct an explanation for why sulfuric acid is...Ch. 5 - Prob. 16ECh. 5 - Prob. 17ECh. 5 - Prob. 18E
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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_forwardDraw the most likely conjugate base resulting from this acid-base reaction. Include all lone pairs. Ignore inorganic byproducts. NaOCH2CH3 Draw Conjugate Base N aarrow_forwardDraw the major organic product of the Bronsted acid-base reaction. Include all lone pairs and charges as appropriate. Ignore any counterions. H I N. NaOH H oarrow_forward
- Draw the products of each proton transfer reaction. Label the acid and base in the starting materials, and the conjugate and base in the products. а. СH,он + NH c. CH;CH2-0-H + H-Br b. CH;CH d. CH;C=C- + H2O + CH;O =arrow_forwardleft 4. Consider the following equilibrium: 29925610 + Aga weak and Sung base Bast CORS + 1ght base: Strong ad d AddOH ress stable OH Is the carboxylate anion (CH3CH₂COO) an appropriate base to deprotonate the alcohol? A) yes, because the equilibrium favors the left side B) yes, because the equilibrium favors the right side C) no, because the equilibrium favors the left side D) no, because the equilibrium favors the right side OH COO basarrow_forwardhydrogens 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_forward
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- 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_forward2. Identify the most acidic compound by labeling it with "M" and the least acidic compound with an "L". Hint: On a separate sheet, draw each conjugate base and assess their stability. NH₂ A OH H₂SO4 3. Which ONE of the following compounds has the highest boiling point? + B CO₂H C HO O OH D Earrow_forwardRank the below compounds in order of increased acidity and explain your choice. HO. H3C || HO. HO.arrow_forward
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