Pushing Electrons
4th Edition
ISBN: 9781133951889
Author: Weeks, Daniel P.
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Videos
Question
Chapter 1, Problem 71EQ
Interpretation Introduction
Interpretation:
The Lewis structures of radicals formed when tert-butyl hydroperoxide breaks homolytically need to be drawn
Concept Introduction:
Covalent bonds can suffer homolytic (symmetrical) bond breaking. During homolytic
cleavage, the electrons of a covalent bond become unpaired and one electron goes
with each fragment. Radicals, rather than ions, are formed. Radicals usually have a
formal charge of zero.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Peroxides are often added to free-radical reactions as initiators because the oxygen–oxygen bond cleaves homolytically rather easily. For example, the bond-dissociation enthalpy of the O¬O bond in hydrogen peroxide (H¬O¬O¬H) is only 213 kJ>mol (51 kcal>mol). Give a mechanism for the hydrogen peroxide-initiated reaction of cyclopentane with chlorine. The BDE for HO¬Cl is 210 kJ>mol (50 kcal>mol).
In the mechanism for the nitration of benzene, what step follows the formation of the nitronium ion (NO2*)?
benzene attacks the nitronium ion to give a sigma complex
O benzene is protonated by nitric acid to give a sigma complex
the sigma complex is deprotonated, thereby restoring aromaticity
a leaving group is ejected, thereby restoring aromaticity
The chlorination of ethane produces many by-products. One by-product that forms in small amounts is 2-chlorobutane.
Suggest a mechanism for the formation of 2-chlorobutane from the radical chlorination of ethane.
(NOTES: intermediates can only have one radical, 2-chlorobutane should be the product of your termination step, any
intermediate radical formed during the propagation phase can be used in the termination step)
Chapter 1 Solutions
Pushing Electrons
Ch. 1 - 1. Hydrogen is a Group I element and each...Ch. 1 - Methanol has the molecular formula CH4O. Its...Ch. 1 - 3. The skeleton of chloromethane is...Ch. 1 - 4. Methanol’s skeleton is
Connecting all bonded...Ch. 1 - 5. The structure for chloromethane is
It...Ch. 1 - Prob. 6EQCh. 1 - 7. Dimethyl ether
No. of electrons in...Ch. 1 - Methylamine (CH5N) No. of electrons in structure...Ch. 1 - Methanethiol (CH4S) No. of electrons in structure...Ch. 1 - Methylal (C3H8O2) No. of electrons in structure...
Ch. 1 - Prob. 11EQCh. 1 - Adding electrons to the skeleton by making single...Ch. 1 - This is done by removing an unshared pair from...Ch. 1 - Prob. 14EQCh. 1 - Prob. 15EQCh. 1 - Prob. 16EQCh. 1 - The skeleton of acetyl chloride is . Write the...Ch. 1 - Three constitutional isomers exist for the formula...Ch. 1 - A number of constitutional isomers exist for the...Ch. 1 - Using the method outlined above, derive the...Ch. 1 - Prob. 21EQCh. 1 - Prob. 22EQCh. 1 - Prob. 23EQCh. 1 - Prob. 24EQCh. 1 - The skeleton of benzyldimethylamine is
The...Ch. 1 - The skeleton is benzaldoxime is The number of...Ch. 1 - Prob. 27EQCh. 1 - Derive Lewis structures for the compounds below....Ch. 1 - Prob. 29EQCh. 1 - Derive Lewis structures for the compounds below....Ch. 1 - Prob. 31EQCh. 1 - Derive Lewis structures for the compounds below....Ch. 1 - The Lewis structure of acetone is Circling the...Ch. 1 - Chloromethane has the Lewis...Ch. 1 - In the Lewis structure for chloromethane, the...Ch. 1 - Prob. 36EQCh. 1 - The oxygen atom in acetone possesses ____ unshared...Ch. 1 - Nitrobenzene has the skeleton
The number of...Ch. 1 - Prob. 39EQCh. 1 - Compute and add on the formal charges I these...Ch. 1 - Prob. 41EQCh. 1 - Prob. 42EQCh. 1 - Prob. 43EQCh. 1 - Prob. 44EQCh. 1 - Prob. 45EQCh. 1 - Prob. 46EQCh. 1 - Prob. 47EQCh. 1 - Compute and add on the formal charges in these...Ch. 1 - Prob. 49EQCh. 1 - Prob. 50EQCh. 1 - The n-propyl cation can be formed from a molecule...Ch. 1 - Prob. 52EQCh. 1 - Prob. 53EQCh. 1 - Methanol, CH3OH, is a compound in which the formal...Ch. 1 - When a proton becomes bonded to diethyl ether, by...Ch. 1 - Tetrahydrofuran has the structure
When a proton...Ch. 1 - Prob. 57EQCh. 1 - Prob. 58EQCh. 1 - The structure of pyridine is
When a proton...Ch. 1 - The carbon atom owns one electron from each of ...Ch. 1 - The n-butyl anion can be formed from When the CLi...Ch. 1 - The isobutyl anion can be formed from When the CNa...Ch. 1 - Prob. 63EQCh. 1 - Ethanol, , is a compound in which the formal...Ch. 1 - The loss of a proton attached to the oxygen atom...Ch. 1 - A very strong base can remove a proton from...Ch. 1 - Prob. 67EQCh. 1 - Prob. 68EQCh. 1 - Prob. 69EQCh. 1 - The homolysis of the OO bond in diacetyl peroxide...Ch. 1 - Prob. 71EQCh. 1 - Prob. 72EQCh. 1 - Prob. 73EQCh. 1 - Prob. 74EQCh. 1 - Prob. 75EQCh. 1 - Heterolytic cleavage of the CO bond to yield a...Ch. 1 - Prob. 77EQCh. 1 - Prob. 78EQCh. 1 - Prob. 79EQCh. 1 - Prob. 80EQ
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
- Alkyl halides can be reduced to alkanes by a radical reaction with tributyltin hydride, (C4H9)3SnH, in the presence of light (hv). Propose a radical chain mechanism by which the reaction might occur. The initiation step is the light-induced homolytic cleavage of the Sn-H bond to yield a tributyltin radical.arrow_forwardCH3 CH3 Br- Br2 CH2CI2 CH3 CH3 H3C H3C Br Electrophilic addition of bromine, Br2, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH2C12. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 Br- .CH3 .CH3 H3C H3C :Br :Br:arrow_forwardRing opening reaction of tetrahydrofuran catalyzed by basic materialsarrow_forward
- The following alcohols react with HBr to afford an alkyl bromide. Based on their structures, indicate if the reaction mechanism is likely to be Sn1 or Sn2arrow_forwardThe mechanism that allows the exothermic hydrolysis of t-butyl chloride to form t-butyl alcohol and chloride ion is as follows: (CH3)3CCl → (CH3)3C+ + Cl− (CH3)3C+ + H2O → (CH3)3COH + H+ Draw the transition state for each step.arrow_forwardDescribe the reaction mechanism for the hydrolysis of 2-bromo-2-methylpropane [CH3C(CH3)2Br] with aqueous hydroxide ions (OH-).arrow_forward
- Two chemists at Dupont found that ICH2ZnI is better than diazomethane at converting a C=C bond to a cylcopropane ring. Propose a mechanism for the reaction, now known as the Simmons–Smith reaction in their honor.arrow_forward1-Suggest a mechanism by which the ozone, O3 is being destructed by the presence of oxygen molecule, O2, and the sun light. 2-Methyl chloride, CH3Cl, is another molecule that destructs the ozone layer. Suggest a mechanism for the destruction of ozone by methyl chloride and the sun light.arrow_forwardThe cis and trans 2-butene stereoisomers have the following rate constant values associated with the electrophilic addition of water in an acid medium at the same temperature. what is the difference between the two values through the energy profile of each reaction. CH3 H,O productos H+ H3C k = 3.51 x 10- M's1 H3C CH3 H,0 > productos H+ k = 8.32 x 10®M's1arrow_forward
- Using fishhook arrows to propose an initiation step for the reaction. Light (hν) induces homolytic cleavage of a weak bond. The Sn-H bond is rather weak and is therefore highly susceptible to homolytic cleavage.arrow_forwardmethanol + CH3OH Suppose you were told that the above reaction was a substitution reaction but you were not told the mechanism. Evaluate the following categories to determine the reaction mechanism and then draw the structure of the major organic product. Type of alkyl halide: Type of nucleophile: Solvent: Is the product racemic?arrow_forwardUse the Text Submission box to answer the following question. Consider the reaction shown below. For a particular concentration of sodium methoxide, the absorbance at 244 nm is measured using UV-vis spectroscopy. Over an initial period, the absorbance at 244 nm increases from 0.50 to 0.60. When the concentration of sodium methoxide is doubled, the absorbance at 244 nm measured after the same initial period is 0.70. What can you conclude about the mechanism of the reaction? NaOCH 3 Amax = 244 nmarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Kinetics: Initial Rates and Integrated Rate Laws; Author: Professor Dave Explains;https://www.youtube.com/watch?v=wYqQCojggyM;License: Standard YouTube License, CC-BY