Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 16.8, Problem 19P
Interpretation Introduction
Interpretation:
How much more stable (in kJ/mol), the benzyl radical when compared to a primary radical, is to be stated. The stability of benzyl and allyl radicals is to be compared.
Concept introduction:
To state:
How much more stable the benzyl radical when compared to a primary radical.
To compare:
The stability of benzyl and allyl radicals.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
MgBr
Mg
C,H,OC,H,
MgBr
o-CH
O *MgBr
C,H,OC,H,
+ CH,OH
H,O, H,SO,
O "MgBr
OH
Data
Glassware oven-dried, assembled, placed under nitrogen (balloon).
Materials: 10 mL anhydrous diethyl ether, 1.0 g Mg turnings. 4.5 mL bromobenzene. 10
mL more anhydrous diethyl ether. 2.5 ml methyl benzoate.
Approximate initiation time: 15 min. Stir 10 min after addition of methyl benzoate.
Transfer reaction mixture to 100 mL Erlenmeyer flask. Rinse reaction flask (2 x 20 mL
diethyl ether).
Acid quench solution: 25 mL 10 % aqueous sulfuric acid/15 g ice.
Saturated NaCI solution: used 20 mL
Hexanes: 20 mL
Isolated: 1.82 g white solid
What is the % yield of the reaction? What is the limiting reagent? Show complete
calculations for the theoretical and % yield calculations
Name ti.. organic compounds:
structure
name
Он
H H H
Н— С — С — С — С — н
|
| || |
н нн н
CH, — сн,-сH, — С -ОН
|
н н
H - C- C = 0
CH3
-
Chapter 16 Solutions
Organic Chemistry
Ch. 16.1 - Prob. 1PCh. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SŪ4. deuterium...Ch. 16.3 - Prob. 5PCh. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P
Ch. 16.4 - Prob. 11PCh. 16.4 - Acetanilide is less reactive than aniline toward...Ch. 16.4 - Prob. 13PCh. 16.5 - At what position would you expect electrophilic...Ch. 16.5 - Show the major product(s) from reaction of the...Ch. 16.6 - The herbicide oxyfluorfen can be prepared by...Ch. 16.7 - Treatment of p-bromotoluene with NaOH at 300°C...Ch. 16.8 - Prob. 18PCh. 16.8 - Prob. 19PCh. 16.8 - Prob. 20PCh. 16.9 - Prob. 21PCh. 16.10 - Prob. 22PCh. 16.10 - Prob. 23PCh. 16.SE - Prob. 24VCCh. 16.SE - The following molecular model of a...Ch. 16.SE - Prob. 26VCCh. 16.SE - Prob. 27VCCh. 16.SE - Aromatic iodination can be carried out with a...Ch. 16.SE - Prob. 29MPCh. 16.SE - The carbocation electrophile in a Friede1-Crafts...Ch. 16.SE - Prob. 31MPCh. 16.SE - The nitroso group, —N=O, is one of the few...Ch. 16.SE - Triphenylmethane can be prepared by reaction of...Ch. 16.SE - Using resonance structures of the intermediates,...Ch. 16.SE - Benzene and alkyl -substituted benzenes can be...Ch. 16.SE - Prob. 36MPCh. 16.SE - Hexachlorophene, a substance used in the...Ch. 16.SE - Benzenediazonium carboxylate decomposes when...Ch. 16.SE - 4-Chloropyridine undergoes reaction with...Ch. 16.SE - Propose a mechanism to account for the following...Ch. 16.SE - In the Gatterman-Kochreaction, a formyl group...Ch. 16.SE - Treatment of p-tert-butylphenol with a strong acid...Ch. 16.SE - Benzyl bromide is converted into benzaldehyde by...Ch. 16.SE - Prob. 44MPCh. 16.SE - Prob. 45MPCh. 16.SE - Prob. 46APCh. 16.SE - Prob. 47APCh. 16.SE - Prob. 48APCh. 16.SE - Predict the major monoalkylation products you...Ch. 16.SE - Name and draw the major product(s) of...Ch. 16.SE - Prob. 51APCh. 16.SE - Prob. 52APCh. 16.SE - What product(s) would you expect to obtain from...Ch. 16.SE - Prob. 54APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 56APCh. 16.SE - Prob. 57APCh. 16.SE - Prob. 58APCh. 16.SE - Prob. 59APCh. 16.SE - Prob. 60APCh. 16.SE - Prob. 61APCh. 16.SE - Prob. 62APCh. 16.SE - Prob. 63APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 65APCh. 16.SE - Prob. 66APCh. 16.SE - Draw resonance structures of the intermediate...Ch. 16.SE - Prob. 68APCh. 16.SE - p-Bromotoluene reacts with potassium amide to give...Ch. 16.SE - Prob. 70APCh. 16.SE - Prob. 71APCh. 16.SE - Prob. 72APCh. 16.SE - Use your knowledge of directing effects, along...Ch. 16.SE - Identify the reagents represented by the letters...Ch. 16.SE - Phenols (ArOH) are relatively acidic, and the...Ch. 16.SE - Prob. 76APCh. 16.SE - Prob. 77APCh. 16.SE - Melamine, used as a fire retardant and a component...
Knowledge Booster
Similar questions
- CI ..*|||| Me CI Br H Br NaOH Acetone CH₂S: DMSO DMF MeOH ONaarrow_forwardConsider the following structures: CH, CH3 H;C, „NH3 H,C, CH H3C, Br H3C. CH CH3 CH3 CH3 JECE CEEJ JEEC СЕЈЕ ЕСЕ Which is a resonance contributor? ECJE Which has a net formal charge of +1? JECE Which has only one type of hydrogen? ECJE Which will form the most stable free radical? JEEC Which is an electrophile? JEECarrow_forwardHi! I found some answers for this question but I am not sure about it.Can you explain the question?arrow_forward
- The compound below is treated with chlorine in the presence of light. H₂C CH3 H₂C CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. Undoarrow_forward11. Compound X, (CH3)2CHCN, can be formed from a haloalkane, C3H7Br.(i) Name compound X............................................................................................................................(ii) Give the reagent and conditions necessary to form X from C3H7Br.Reagent..............................................................................................................Conditions..........................................................................................................(iii) Name and outline the mechanism for this reaction, showing clearly the structure of C3H7Br.Name of mechanism..........................................................................................Mechanism.arrow_forward= O PRINCIPLES OF ORGANIC CHEMISTRY Identifying rigid parts of an acyclic organic molecule In the actual molecule of which this is a Lewis structure, which of the labeled distances can change? marked 10 H O H B G1C F H A N E unmarked C O H List all the distances that can change. For example, suppose all the distances were measured at a certain time, and again 0.1s later. If distance A might be 50% bigger or smaller the second time, but all the other distances are certain to be the same, you should write "A". If A and B might be different the second time, but no other distances, you would write "A, B". And so on. Note for advanced students: you can assume the molecule is dissolved in an appropriate solvent at room temperature. 00.... X 90/5 You can click the "unmarked" tab to see the molecule without any of the distances marked. 5 Jaarrow_forward
- Please send me the question in 20 minutes it's very urgent plz findarrow_forwardAnswer properlyarrow_forwardA glycerol molecule and three butyric acid molecules are shown. Delete atoms and add bonds as necessary to form a triacylglycerol (triglyceride). Draw only the triacylglycerol product. Select Draw Rings More Erase / |||||| COH G H H н-с H Ć H O H H H I O —1 O HO ||| C H₂ UI H₂ с H₂ с H₂ CH CH3 CH₂ Q2 Qarrow_forward
- The enthalpy for hydrogenation of different isomers of butene is shown in the following figure. Which statement below best interprets this figure? Hy I3D H2 7k mot 5kJ mot + H2 AH-120 kJ mot AH"-127 kJ mot AH-115 kJ mot © GMU 2020 Stability and hydrogenation enthalpies are not correlated. Butene II is less stable than butene I by 7 kJ/mol. O Butene Il is 7 kJ/mol more stable than I and 5 kJ/mol more stable than III. Butene II is 5 kJ/mol less atable than butene IlI. Enthalpyarrow_forwardIn the space below, draw the three monochlorination products resulting from the radical chlorination of chlorocyclopentane. CI Cl₂ heat Based on your results for the radical chlorination experiment, predict which products would be most and least abundant in the product mixture. Briefly justify your answer.arrow_forwardPlease explain and solve very correctlyarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Chemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning