Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 21, Problem 21.42P
(a)
Interpretation Introduction
Interpretation:
The heat of the reaction is to be calculated.
Concept introduction:
The heat of the reaction is calculated using following formula,
(b)
Interpretation Introduction
Interpretation:
The chain propagation step is to be written and the net result of each pair of the reaction is to be shown
(C)
Interpretation Introduction
Interpretation:
The heat of the reaction is to be calculated for the propagation step.
Concept introduction:
The heat of the reaction is calculated using following formula,
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(b)
Addition of HBr to the alkene in the presence of peroxide form radical
intermediates. Based on the following reaction, use the curved arrows to
HBr
B (preferred product)
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(i)
show the initiation step of this reaction.
(ii)
draw the possible structures of the two radicals formed in the
propagation step.
(ii)
explain the formation of the preferred product B.
Resveratrol is an antioxidant found in the skin of red grapes. Its anticancer, anti-inflammatory, and various cardiovascular effects are under active investigation. (a) Draw all resonance structures for the radical that results from homolysis of the OH bond shown in red. (b) Explain why homolysis of this OH bond is preferred to homolysis of either OH bond in the other benzene ring.
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Chapter 21 Solutions
Organic Chemistry
Ch. 21.2 - Construct a Frost circle for a planar...Ch. 21.2 - Which compound gives a signal in the 1H-NMR...Ch. 21.2 - Prob. 21.3PCh. 21.2 - Prob. 21.4PCh. 21.3 - Prob. 21.5PCh. 21.4 - Arrange these compounds in order of increasing...Ch. 21.4 - Prob. AQCh. 21.4 - Prob. BQCh. 21.4 - Prob. CQCh. 21.5 - Prob. 21.7P
Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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- Propylene does not undergo free radical polymerization readily because there are two competing steps after initiation: propagation and hydrogen atom abstraction.(a) Using a generic radical R• as a reactant with propylene, draw the mechanism and products for the two competing steps.(b) Which step produces the more stable product?(c) How do your results explain propylene’s poor reactivity in free radical polymerization?arrow_forward(3) HI does not undergo free radical addition with 1-butene, even in the presence of a peroxide. Please provide an explanation by analyzing the propagation steps if the same radical reaction occurred with HI. Besides the bond dissociation enthalpies in the appendix, the following approximate bond dissociate enthalpies might be useful to you: ~310 kJ/mol The component of C=C CH3CH₂CH₂CH₂-Br CH3CH₂CH₂CH2-I -290 kJ/mol (C-Br bond) ~235 kJ/mol (C-I bond)arrow_forwardPGF2α (Section 4.15) is synthesized in cells using a cyclooxygenase enzyme that catalyzes a multistep radical pathway. Two steps in the pathway are depicted in the accompanying equations. (a) Draw in curved arrows to illustrate how C is converted to D in Step [1]. (b) Identify Y, the product of Step [2], using the curved arrows that are drawn on compound D.arrow_forward
- 1) The carbon-oxygen double bond present in aldehydes and ketones is very polar. What does this mean and how does it arise? 2) The carbon-oxygen double bond is readily attacked by nucleophiles like cyanide ions or ammonia. (i) What do you understand by the term nucleophile? (ii) Which part of the carbon-oxygen double bond is attractive to nucleophiles? 3) Why is there a difference between aldehydes and ketones in their response to oxidizing agents such as potassium dichromate(VI) solution acidified with dilute sulfuric acid?arrow_forward• H2O Based on the reaction above, (a) Outline the reaction mechanism. (b) Sketch the energy diagram. (c) Give the rate equation. (d) Explain what happens to the reaction rate if: The leaving group is changed to I. (0) (a) The solvent is changed to DMF. The alkyl halide is changed to (v) The concentration of the solvent is increased by five-fold answer with proper justification and with good explanationarrow_forwardThe rate law for addition of Br2 to an alkene is first orderin Br2 and first order in the alkene. Does this informationsuggest that the mechanism of addition of Br2 to analkene proceeds in the same manner as for addition of HBr?Explain.arrow_forward
- Resveratrol is an antioxidant found in the skin of red grapes. Its anticancer, anti-inammatory, and various cardiovascular effects are under active investigation. (a) Draw all resonance structures for the radical that results from homolysis of the OH bond shown in red. (b) Explain why homolysis of this OH bond is preferred to homolysis of either OH bond in the other benzene ring.arrow_forward(c)Show step by step how to synthesize methoxybenzene from benzene.arrow_forwarda) The alkene drawn here undergoes an electrophilic addition reaction with HBr. Ś i) Give the IUPAC name of this molecule. ii) Outline the mechanism of this reaction. Your mechanism should show the formation of BOTH possible products and should also name both products. iii) Explain why the Markovnikov rule does not predict a major product in this case. b) The common name of the molecule drawn below is diisopropyl ether. Its structural formula is (CH3)2CHOH(CH3)2. tot It can be synthesized in two steps using the starting materials propan-2-ol, 2-chloropropane and sodium metal. One of these steps is a nucleophilic substitution reaction. i) Using structural formulae, write two balanced chemical equations representing the two steps of this synthesis. No state symbols are required. ii) Outline the mechanism of the nucleophilic substitution step.arrow_forward
- When HBr adds to (CH3)2C = CH2 under radical conditions, two radicals are possible products in the first step of chain propagation. Draw the structure of both radicals and indicate which one is formed. Then draw the preferred product from HBr addition under radical conditions.arrow_forwardUse bond-dissociation enthalpies (Table 4-2, p. 167) to calculate values of ∆H° for the following reactions. (a) CH3¬CH3 + I2 ¡ CH3CH2I + HI(b) CH3CH2Cl + HI ¡ CH3CH2I + HCl(c) (CH3)3C¬OH + HCl ¡ (CH3)3C¬Cl + H2O (d) CH3CH2CH3 + H2 ¡ CH3CH3 + CH4 (e) CH3CH2OH + HBr ¡ CH3CH2¬Br + H2Oarrow_forwardThe rate law for addition of Br2Br2 to an alkene is first order in Br2Br2 and first order in the alkene. Does this information suggest that the mechanism of addition of Br2Br2 to an alkene proceeds in the same manner as for addition of HBr? Explain.arrow_forward
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