ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
2nd Edition
ISBN: 9780393664034
Author: KARTY
Publisher: NORTON
expand_more
expand_more
format_list_bulleted
Question
Chapter 6, Problem 6.52P
Interpretation Introduction
Interpretation:
It is to be determined in which of the four molecules A-D the pKa value of the OH proton is expected to be most similar to that of cyclohexanol.
Concept introduction:
The acidity of a proton depends primarily on the functional group to which it belongs. Nearby structural features can modify the acidity. A highly electronegative atom such as fluorine or oxygen on an adjacent carbon can significantly change the pKa. Another feature than can modify the acidity of a proton is a double bond on the carbon to which the proton is attached. Both features increase the acidity of the proton, reducing its pKa value.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The acid dissociation constant (Ka) for loss of a proton from cyclohexanol is 1 X10-16.
a. Draw a reaction coordinate diagram for loss of a proton from cyclohexanol.
4-t-butylcyclohexanone was transformed to cis and trans-4-t-butylcyclohexanol using NaBH4. How can we tell that the trans isomer is prefered from the following NMRs? Make sure to explain why the product distribution occurs in the reaction. (PICTURE that says 1H is the same NMR just zoomed).
The 1H NMR spectra for two esters with molecular formula C8H8O2 are shown next. Which of the esters is hydrolyzed more rapidly in an aqueous solution with a pH of 10?
Chapter 6 Solutions
ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
Ch. 6 - Prob. 6.1PCh. 6 - Prob. 6.2PCh. 6 - Prob. 6.3PCh. 6 - Prob. 6.4PCh. 6 - Prob. 6.5PCh. 6 - Prob. 6.6PCh. 6 - Prob. 6.7PCh. 6 - Prob. 6.8PCh. 6 - Prob. 6.9PCh. 6 - Prob. 6.10P
Ch. 6 - Prob. 6.11PCh. 6 - Prob. 6.12PCh. 6 - Prob. 6.13PCh. 6 - Prob. 6.14PCh. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Prob. 6.17PCh. 6 - Prob. 6.18PCh. 6 - Prob. 6.19PCh. 6 - Prob. 6.20PCh. 6 - Prob. 6.21PCh. 6 - Prob. 6.22PCh. 6 - Prob. 6.23PCh. 6 - Prob. 6.24PCh. 6 - Prob. 6.25PCh. 6 - Prob. 6.26PCh. 6 - Prob. 6.27PCh. 6 - Prob. 6.28PCh. 6 - Prob. 6.29PCh. 6 - Prob. 6.30PCh. 6 - Prob. 6.31PCh. 6 - Prob. 6.32PCh. 6 - Prob. 6.33PCh. 6 - Prob. 6.34PCh. 6 - Prob. 6.35PCh. 6 - Prob. 6.36PCh. 6 - Prob. 6.37PCh. 6 - Prob. 6.38PCh. 6 - Prob. 6.39PCh. 6 - Prob. 6.40PCh. 6 - Prob. 6.41PCh. 6 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - Prob. 6.44PCh. 6 - Prob. 6.45PCh. 6 - Prob. 6.46PCh. 6 - Prob. 6.47PCh. 6 - Prob. 6.48PCh. 6 - Prob. 6.49PCh. 6 - Prob. 6.50PCh. 6 - Prob. 6.51PCh. 6 - Prob. 6.52PCh. 6 - Prob. 6.53PCh. 6 - Prob. 6.54PCh. 6 - Prob. 6.55PCh. 6 - Prob. 6.56PCh. 6 - Prob. 6.57PCh. 6 - Prob. 6.58PCh. 6 - Prob. 6.59PCh. 6 - Prob. 6.60PCh. 6 - Prob. 6.61PCh. 6 - Prob. 6.62PCh. 6 - Prob. 6.63PCh. 6 - Prob. 6.64PCh. 6 - Prob. 6.65PCh. 6 - Prob. 6.66PCh. 6 - Prob. 6.67PCh. 6 - Prob. 6.68PCh. 6 - Prob. 6.69PCh. 6 - Prob. 6.70PCh. 6 - Prob. 6.71PCh. 6 - Prob. 6.72PCh. 6 - Prob. 6.73PCh. 6 - Prob. 6.74PCh. 6 - Prob. 6.75PCh. 6 - Prob. 6.76PCh. 6 - Prob. 6.77PCh. 6 - Prob. 6.78PCh. 6 - Prob. 6.79PCh. 6 - Prob. 6.80PCh. 6 - Prob. 6.81PCh. 6 - Prob. 6.82PCh. 6 - Prob. 6.83PCh. 6 - Prob. 6.84PCh. 6 - Prob. 6.85PCh. 6 - Prob. 6.86PCh. 6 - Prob. 6.87PCh. 6 - Prob. 6.88PCh. 6 - Prob. 6.1YTCh. 6 - Prob. 6.2YTCh. 6 - Prob. 6.3YTCh. 6 - Prob. 6.4YTCh. 6 - Prob. 6.5YTCh. 6 - Prob. 6.6YTCh. 6 - Prob. 6.7YTCh. 6 - Prob. 6.8YTCh. 6 - Prob. 6.9YTCh. 6 - Prob. 6.10YTCh. 6 - Prob. 6.11YTCh. 6 - Prob. 6.12YTCh. 6 - Prob. 6.13YTCh. 6 - Prob. 6.14YTCh. 6 - Prob. 6.15YTCh. 6 - Prob. 6.16YTCh. 6 - Prob. 6.17YTCh. 6 - Prob. 6.18YTCh. 6 - Prob. 6.19YTCh. 6 - Prob. 6.20YT
Knowledge Booster
Similar questions
- Phenols generally have lower pKa’s than aliphatic alcohols because of resonance stabilization with the aromatic ring. Draw all of the resonance contributors for the phenolate ions below. Make note of how the substituents either stabilize or destabilize the system.arrow_forwardAn allylic halide with the chemical formula C5H9Cl undergoes an SN1 reaction with water to produce B and C, two isomeric products. What would be the structure of the allylic halide and the products B and C? What peaks correspond with what protons in B and C?arrow_forwarda. Compound X is benzene, Y is acetic anhydride acid. Complete the following scheme and determine Z! b. Determine which reagents except acetic acid anhydrides can replace Y!arrow_forward
- Which structural effect predominantly accounts for each given observation or phenomenon. Choose your answers from the following: A = Resonance B = C-H hyperconjugation C = Inductive Effect D = Steric Effect The carbinol carbon (one where the -OH group of an alcohol is bonded to) is electrophilic.arrow_forwardI'm not sure how to approach this problem. Do I look at the EWG's and EDG's of the substiuents in the products, or find the pka value of each product? please explain so I can do it myselfarrow_forwardGiven the following compounds and boiling points: Determine the IMFs Order the compounds from weakest to strongest IMFs, and Pentane (C5H12) 36°C Methane (CH4) -164°C Sodium n-butoxide (C4H9NaO) +260°C Hydrogen dioxide (H2O) 100°Carrow_forward
- Consider the series of the trans effect: CO, CN-, C2H4 > PR3, H-, CH3- > C6H5- > NO2-, SCN-, I- > Br- >Cl- > py > NH3 > H20 What would be the major product of the following reaction? Select one:arrow_forwardUsing your knowledge of general chemistry and organic chemistry, answer the following questions: Predict the relative acidities within each of the following groups, then identify the conjugate bases, and finally predict their relative leaving group abilities HClO3 and HClO2 PH3 and H2S [NH4]+ and [H3O]+ Explain why the trifluoromethane sulfonate (TfO-) ion is a better leaving group than the methanesulfonate (MsO-) ion.arrow_forwardIf you have to characterize the reduction product of 3-nitroacetophenone using NaBH4 by 1H NMR, what changes would you expect? Hint: Draw the structure of both starting compounds and products and predict the number of peaks.arrow_forward
- In the acid-catalyzed dehydration of 2-methyl-1-propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon–oxygen bond in the alkyloxonium ion? What ion would be formed as a result of a methyl shift? Which pathway do you think will predominate, a hydride shift or a methyl shift?arrow_forwardIdentify which structural effect predominantly accounts for each given observation or phenomenon. Choose your answers from the following: A = Resonance B = C-H hyperconjugation C = Inductive Effect D = Steric Effect The benzyl and allylic carbocations are stable.arrow_forwardThe following pKa values have been measured. Explain why a hydroxyl group in the para position decreases the acidity while a hydroxyl group in the meta position increases the acidity.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you