11. Consider the pKa values (for the bolded H) in the structures below. HO HO, pKa = ~10 pKa = ~17 pKa = ~4 %3D %3D %3D Explain these differences in the pka values. (Hint: Draw each molecule if it was deprotonated. The more stable the deprotonated structure is means it is easier to deprotonate, and therefore the more acidic (lower pKa) the molecule! Consider resonance structures for the deprotonated structures to help explain the differences in pKa. HOeM HO de anolisest S kr abubal woR

11. Consider the pKa values (for the bolded H) in the structures below. HO HO, pKa = ~10 pKa = ~17 pKa = ~4 %3D %3D %3D Explain these differences in the pka values. (Hint: Draw each molecule if it was deprotonated. The more stable the deprotonated structure is means it is easier to deprotonate, and therefore the more acidic (lower pKa) the molecule! Consider resonance structures for the deprotonated structures to help explain the differences in pKa. HOeM HO de anolisest S kr abubal woR

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter13: Substitution

Section: Chapter Questions

Problem 29CTQ

See similar textbooks

Similar questions

C341 Chapters (Acid-base chemistry) 9.) Acid-base equilibrium. For each reaction, perform the following tasks: a.) Complete the following reactions using the appropriate curved arrows to demonstrate the flow of electrons pairs in each potential reaction. b.) Indicate if the reaction lies to the right or the left (circle the correct arrow direction). c.) Calculate an approximate Ken for each reaction. d.) Write the pKa values under each acid, so we can evaluate your progress better and award partial credit. d.) Finally, label the acid (A), base (B), conjugate acid (CA) and base (CB) correctly based on the direction you decided. Keq = Direction: OH eg HO Keq = Direction: Keq = Direction: LOH OH ONa لها LIⒸ CHgLi Page 5 of 7
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] ? ChemDoodle
From each pair, select the stronger base. Then draw the conjugate acid of the strong base below. CH3CH20 or CH3CEC • 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. C opy aste
Draw the structure of the product of the reaction between the compound shown below and H2SO4- CH3CH2OH • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. the reaction involves proton transfer, draw the products in separate sketchers. If the reaction is a Lewis acid-base reaction, draw the product in one sketcher only. Visited C aste opy ChemDoodle® >
Given 4-methylhexanoic acid1. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH> pKa? 2. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH = pKa? 3. How will the acid be deprotonated if the pH the solution is adjusted so that pH <pKa?
Draw the products of the following reactions (place the correct charges when necessary). Then, using the pkas values of each molecues, use a pka argument to assess whether the reaction can be considered irreversible or at the equilibrium. NaH H2SO4 ①O-I H__H NH Y ОН < ОН
Which of the compounds shown below is the most acidic hydrogen and what is the approximate pKa value?
|2. Give the major organic products expected in each of the following reactions. (h) он CH Na,Cr,O7 H,SO, H,Cro, H,0 PHCH,OH Cros pyridine Ph. OH (k) 1. Ph,P 2. Buli Ph (CH,),CH̟I 3. A
9. Rank the following compounds in order of increasing acidity (least acidic < most acidic) [R is an alkyl group and X is Cl, Br, or I]. a. <<< IV b. IV << | < | c. I
Rank compounds L-P in order of decreasing acid strength, from lowest pk, to highest pka. Explain. L M
Calculate pk, values for the following acids. (Enter your answer to three significant figures.) a. Hydrocyanic acid, HCN (K₂ = 4.90x10-10): b. Ethanol (K = 1.00×10-16):
20 Arrange these acids according to their expected pKą values. CICH₂CH₂COOH СІСН,СООН Highest pKa Lowest pKa Answer Bank Cl₂CHCOOH CH₂CH₂COOH