Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 4, Problem 4.58SP
lodination of
The following bond-dissociation energies may be helpful:
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Using the table of average bond dissociation enthalpies at 25°C, determine which of the following reactions are energetically favorable at room temperature. Assume that ▲S = 0.
Q.CH2=CH2 + CH4 --> CH3CH2CH3
is steric hinderance not an issue here? why when reacting with KOC(CH3)3 does it yield 2-isopropyl-1-pentene and it yields 2,3-dimethyl-2hexene here?
Consider the following statement in reference to SN1, SN2, E1, and E2 reactions of haloalkanes. To which mechanism(s), if any, does the statement apply?
Order of reactivity of haloalkanes is 3°> 2°> 1°.
Chapter 4 Solutions
Organic Chemistry (9th Edition)
Ch. 4.3A - Draw Lewis structures for the following free...Ch. 4.3B - a. Write the propagation steps leading to the...Ch. 4.3C - Prob. 4.3PCh. 4.3C - Prob. 4.4PCh. 4.4 - The following reaction has a value of G =...Ch. 4.4 - Under base-catalyzed conditions two molecules of...Ch. 4.5B - When ethene is mixed with hydrogen in the presence...Ch. 4.5B - For each reaction, estimate whether S for the...Ch. 4.7 - a. Propose a mechanism for the free radical...Ch. 4.7 - a. Using bond-dissociation enthalpies from...
Ch. 4.8 - The reaction of tert-butyl chloride with methanol...Ch. 4.8 - Under certain conditions, the bromination of...Ch. 4.8 - When a small piece of plat num is added to a...Ch. 4.10 - Prob. 4.14PCh. 4.10 - Prob. 4.15PCh. 4.12 - The bromination of methane proceeds through the...Ch. 4.12 - a. Using me BDEs in Table4-2 (page 167 ), compute...Ch. 4.13A - What would be the product ratio in the...Ch. 4.13A - Classify each hydrogen atom in the following...Ch. 4.13B - Use the bond-dissociation enthalpies in Tabte4-2...Ch. 4.13B - Prob. 4.21PCh. 4.13B - Prob. 4.22PCh. 4.14 - a. Compute the heats of reaction for abstraction...Ch. 4.14 - 2,3-Dimethylbutane reacts with bromine in the...Ch. 4.14 - Prob. 4.25PCh. 4.15 - Prob. 4.26PCh. 4.15 - Prob. 4.27PCh. 4.16A - Prob. 4.28PCh. 4.16A - Prob. 4.29PCh. 4.16B - Prob. 4.30PCh. 4.16C - Prob. 4.31PCh. 4.16C - Acetonitrile (CH3C N) is deprotonated by very...Ch. 4.16D - Prob. 4.33PCh. 4 - The following reaction is a common synthesis used...Ch. 4 - Consider the following reaction-energy diagram. a....Ch. 4 - Draw a reaction-energy diagram for a one-step...Ch. 4 - Draw a reaction-energy diagram for a two-step...Ch. 4 - Prob. 4.38SPCh. 4 - Treatment of tert-butyl alcohol with concentrated...Ch. 4 - Label each hydrogen atom in the following...Ch. 4 - Prob. 4.41SPCh. 4 - Prob. 4.42SPCh. 4 - Prob. 4.43SPCh. 4 - Prob. 4.44SPCh. 4 - Prob. 4.45SPCh. 4 - Prob. 4.46SPCh. 4 - For each compound, predict the major product of...Ch. 4 - When exactly 1 mole of methane is mixed with...Ch. 4 - Prob. 4.49SPCh. 4 - Prob. 4.50SPCh. 4 - Prob. 4.51SPCh. 4 - When dichloromethane is treated with strong NaOH,...Ch. 4 - Prob. 4.53SPCh. 4 - When a small amount of iodine is added to a...Ch. 4 - Prob. 4.55SPCh. 4 - When healthy, Earths stratosphere contains a low...Ch. 4 - Prob. 4.57SPCh. 4 - lodination of alkanes using iodine (I2) is usually...
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- In light of the fact that tertiary alkyl halides undergo spontaneous dissociation to yield a carbocation plus halide ion (see Problem 10-45), propose a mechanism for the following reaction.arrow_forwardFollowing is a balanced equation for the allylic bromination of propene. CH2==CHCH3 + Br2 h CH2==CHCH2Br + HBr (a) Calculate the heat of reaction, H 0, for this conversion. (b) Propose a pair of chain propagation steps and show that they add up to the observed stoichiometry. (c) Calculate the H 0 for each chain propagation step and show that they add up to the observed H 0 for the overall reaction.arrow_forwardPredict the products for the hydrohalogenation reaction of 1-methyl-1,3-cyclohexadiene with 1 equivalent of HBr in thermodynamic conditions.arrow_forward
- The reaction of 2,2-dimethyl-1-propanol [(CH3)3CCH2OH], also known by the common name neopentyl alcohol, with HBr is very slow and gives 2-bromo-2-methylbutane as the major product.Give a mechanistic explanation for these observations.arrow_forwardAs we will learn, many antioxidants–compounds that prevent unwanted radical oxidation reactions from occurring–are phenols, compounds that contain an OH group bonded directly to a benzene ring.a.) Explain why homolysis of the O–H bond in phenol requiresconsiderably less energy than homolysis of the O–H bond in ethanol(362 kJ/mol vs. 438 kJ/mol).b.) Why is the C–O bond in phenol shorter than the C–O bond in ethanol?arrow_forwardFollowing is a balanced equation for bromination of toluene. (a) Using the values for bond dissociation enthalpies given in Appendix 3, calculate H0 for this reaction. (b) Propose a pair of chain propagation steps and show that they add up to the observed reaction. (c) Calculate H0 for each chain propagation step. (d) Which propagation step is rate-determining?arrow_forward
- Propose a mechanism for the free-radical chlorination of ethane,CH3¬CH3 + Cl2 ¡hv CH3¬CH2Cl + HClarrow_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_forwardFor each reaction below, provide the structural formula for the reactants and the predicted products. Indicate which mechanism the reaction will follow and use curved arrow formalism to illustrate the predicted reaction mechanism. t-butylalcohol + NaBr ?arrow_forward
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