Organic Chemistry: Principles And Mechanisms
2nd Edition
ISBN: 9780393663549
Author: KARTY, Joel
Publisher: W. W. Norton and Company
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 6, Problem 6.28P
Interpretation Introduction
Interpretation:
Out of the two resonance structures A and B, it is to be determined which one contributes more to the hybrid.
Concept introduction:
How well an atom accommodates a charge depends on its electronegativity. An atom with high electronegativity can better accommodate a negative charge while an atom with low electronegativity can better accommodate a positive charge.
The resonance structure in which positive charge is available on less electronegative atom and negative charge is available on more electronegative atom, contributes more to the resonance hybrid.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
I have a question here so in essence were just comparing the electronegativity values that are being given, soC and Cl, C and O, C and H to determine the partially positive, partially negative charges? So option I: Cl and C, option 2 O and C, option III C on its own correct?
Draw the less stable chair conformation of myo-inositol clearly indicating the axial and equatorial substituents as well as the cis and trans relationships of at least 3 OH groups.
Draw a viable Newman Projection using any carbon carbon bond clearly showing a gauche interaction between the substituents.
5. What is the product for the following reaction
for each step
and draw the mechanism
H
1. NaNH2
2, EtBr
Chapter 6 Solutions
Organic Chemistry: Principles And Mechanisms
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
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- mical lation or mula trations, AAAAAAAAAAAAA Experiment #8 Electrical conductivity & Electrolytes Conductivity of solutions FLINN Scientific conductivity meter scale - RED LED Scale 0 Green LED OFF OFF 1 Dim OFF 2 medium OFF Bright Dim 4 Very Bright Medium 3 LED Conductivity Low or None' Low Medium High very high SE = Strong Electrolyte, FE = Fair Electrolyte WE Weak Electrolyte, NE= Noni Electrolyte 9 0.1 M NaOH. 10. 0.1M NH3 11. D.1M HCT 12. 0.1 M HC2H3D2 13 0 m H2SO4 Prediction observed conductivity ? Very bright red, dim green (4) ? Saturated Bright red, dim green 3 Cacal) Bright red, dim green 3 Prediction Bright red, No green ? observed Bright red,dim green ? Conductivity Just red? I Can you help me understand how I'm supposed to find the predictions of the following solutions? I know this is an Ionic compound and that the more ions in a solution means it is able to carry a charge, right? AAAAAA The light are not matching up with the scale So I'm confused about what I should be…arrow_forwardLabel these peaks in H- NMR and C- NMRarrow_forwardComplete the following table. The only density needed is already given. Show your calculations in a neat and easy-to-follow manner in the space below the table. All units should be included and significant figures should be given close attention. Be sure to notice that the amount of material should be in millimoles rather than moles, and the theoretical mass of the product should in milligrams rather than grams. LOCH 3 + H2SO4 HNO 3 O=C-OCH 3 NO2 x H₂O F.W. 4.0 mL 1.3 M amount 0.50 mL in H2SO4 mg Theoretical Theoretical mmoles density 1.09arrow_forward
- Kumada Coupling: 1. m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a mechanism and give two reasons why you would NOT get the desired product. Draw the reaction (NOT a mechanism) for a Kumada coupling to produce the molecule above from m-dichlorobenzene. Calculate the theoretical yield for the reaction in question 2 using 1.5 g of p-dichlorobenzene and 3.0 mL isobutyl bromide. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardWintergreen from Aspirin: 1. In isolating the salicylic acid, why is it important to press out as much of the water as possible? 2. Write the mechanism of the esterification reaction you did. 3. What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional group change. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardSynthesis of ZybanⓇ: 1. Write a mechanism for the bromination of m-chloropropiophenone. Br₂ CH2Cl2 Cl Br 2. Give the expected m/z (to a round number) for the molecular ion from the product above (including isotopic peaks). 3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forward
- Synthesis of Ibuprofen-Part 2: 1. Some pain relievers including ibuprofen (MotrinⓇ) and naproxen (Aleve®) are "α-arylpropanoic acids." Look up the structure of naproxen (AleveⓇ), another a-arylpropionic acid. Using the same reactions that we used for making ibuprofen, show how to make naproxen from the compound below. Show all intermediates and reagents in your synthesis. Show how you would prepare ibuprofen starting from p-isobutylbenzene rather than p-isobutylacetophenenone. What reaction steps would need to change/add? 3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAcid Catalyzed Aromatization of Carvone: 1. Starting with the ketone, below, draw a mechanism for the reaction to give the phenol as shown. H2SO4 HO- H₂O 2. Why do we use CDCl instead of CHCl, for acquiring our NMR spectra? 3. Why does it not matter which enantiomer of carvone is used for this reaction? What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAssign this H NMRarrow_forward
- Please complete these blanks need that asaparrow_forwardNitration of Methyl Benzoate: 1. Predict the major product for the reaction below AND provide a mechanism. Include ALL resonance structures for the intermediate. C(CH3)3 NO₂* ? 2. Assuming the stoichiometry is 1:1 for the reaction above, what volume of concentrated nitric acid would be required to mononitrate 0.50 grams of the compound above? What product(s) might you expect if you nitrated phenol instead of methyl benzoate? Explain your reasoning. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardSodium Borohydride Reduction (continued on the next page): 1. Draw the product of each of the reactions below and give the formula mass to the nearest whole number. ? (1) NaBH (2) acid (1) NaBD4 (2) acid ? 2. In mass spectra, alcohols typically break as shown in equation 8 in chapter 11 (refer to your lab manual). The larger group is generally lost and this gives rise to the base peak in the mass spectrum. For the products of each of the reactions in question # 1, draw the ion corresponding to the base peak for that product and give its mass to charge ratio (m/z). 3. Given the reaction below, calculate how many mg of 1-phenyl-1-butanol that can be produced using 31 mg NaBH4 and an excess of butyrophenone. 4. + NaBH4 OH (after workup with dilute HCI) What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning