AICI,HCI2.H2SO4H20HO"130°h = SN1 Nucleophilic substitutioni= Sy2 Nucleophilic substitutiona = Proton transfere = Electrophilic additionb = Lewis acid/basec = Radical chain substitutionf= El Eliminationg = E2 Eliminationj= Electrophilic aromatic substitutiond = Radical chain additionIdentify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for youranswers.1.2.

Organic reactions are classified mainly as addition (if a reagent gets added to the carbon carbon…

1. AICI, + HCI 2. H2SO4 он H20 130° a = Proton transfer e = Electrophilic addition h = Sy1 Nucleophilic substitution b= Lewis acid/base f= El Elimination i= Sy2 Nucleophilic substitution c = Radical chain substitution d = Radical chain addition g= E2 Elimination j = Electrophilic aromatic substitution Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for your answers.

1. AICI, + HCI 2. H2SO4 он H20 130° a = Proton transfer e = Electrophilic addition h = Sy1 Nucleophilic substitution b= Lewis acid/base f= El Elimination i= Sy2 Nucleophilic substitution c = Radical chain substitution d = Radical chain addition g= E2 Elimination j = Electrophilic aromatic substitution Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for your answers.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter8: Haloalkanes, Halogenation, And Radical Reactions

Section: Chapter Questions

Problem 8.21P

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In SN2 reactions of haloalkanes, the order of reactivity is RI>RBr>RCl>RF. Alkyl iodides are considerably more reactive than alkyl fluorides, often by factors as great as 106. All 1-halo-2,4-dinitrobenzenes, however, react at approximately the same rate in nucleophilic aromatic substitutions. Account for this difference in relative reactivities.
[Review Topics] [References] Br H3C CH3 H3C H3C 1. Aqueous ethanol + HO +] H. CH3 H. CH3 BH3 O-BH3 f=Sn1 Nucleophilic substitution g = Sn2 Nucleophilic substitution a = Proton transfer d = El Elimination b Lewis acid/base e = E2 Elimination c = Electrophilic addition The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - gf answers. 2.
[Review Topics] [References] HO pyridine 1. SOCIl, + sO2 + H. Aqueous acetone H3C H20 H3C HBr 2. Br H OH optically active racemic f = SN1 Nucleophilic substitution g = SN2 Nucleophilic substitution a = Proton transfer d = E1 Elimination b = Lewis acid/base e = E2 Elimination c = Electrophilic addition The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - g for your answers. 1. 2.
Fill in the table with the partial charges of the atoms. The atoms are numbered with the following scheme with respect to the substituent on the aromatic ring. x c/ 3. | H./ Atom Chlorobenzene Nitrobenzene Aminobenzene C2 Ca Which substituent results in a ring atom with the greatest positive charge (smallest negative charges)? What is the mechanism that causes this pattern of electron distribution on the aromatic ring? Diagram the mechanism. Which substituent results in a ring atom with the least positive charge (largest negative charges)? What is the mechanism that causes this pattern of electron distribution on the aromatic ring? Diagram the mechanism.
CCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*
Hydroboration of Alkenes vs. Alkynes. Addition of an alkylboranes to a carbon- carbon double bond ("hydroboration") followed by oxidation is a common way to alcohols, for example, addition of dimethylborane to 2,3-dimethyl-2-butene yields 2,3-dimethyl-2-butanol. Me₂BH + Me₂C=CMe₂- →→ Me₂CH-CMe₂OH The reaction is more general as borane also adds to carbon-carbon triple bonds. obtain structures and energies for reactants and transition states for addition of dimethylborane (Me₂BH) to both ethylene and acetylene. Which reaction has the lower activation energy? Offer an explanation for your result.
All electrophilic aromatic substitution reactions occur via a two-step mechanism: addition of the electrophile to form a resonance-stabilized carbocation, followed by deprotonation by a base. In the step shown below, loss of a proton to form the substitution product was drawn using the resonance structure with the + 1 formal charge at the ortho position to the carbon bonded to the electrophile. Redraw the step shown with the other two resonance structures and use curved arrows to show how these other two resonance structures can be converted to the substitution product by removal of a proton with the base shown. Part: 0/2 Part 1 of 2 H :CI-AICI, Draw the mechanism that generates the final substitution product with the +1 formal charge at the para position. Cl HC1 AICI3
C=CH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-OH HO: Hjö: C=CH c=CH Hö Hg Hg
b) Fill in the gaps by drawing the structures of the missing reagents, intermediates and/or products of the following electrophilic aromatic substitutions. Chemical formulas have been added for guidance. Step 1 Step 2 CH3 HNO3 H2 1. C6H5NO2 C,HgN H2SO4 `NO2 Pd/C 1 2 4 CH3 Br2/FeBr3 C3H;Bro 5 6 Using resonance structures, justify whether the acetyl group of compound 5 will direct the bromination reaction to the meta or ortho/para positions.
CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, 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 CH,Cl,. 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 CH3 CH3 H3C H3C :Br: :Br:
Functional groups such as alkynes react the same in complex molecules as they do in simpler structures. The following example of alkyne reaction were taken from syntheses carried out in the research group of E. J. Corey at Harvard University. You can assume that the reactions listed involve only the alkyne, not any of the functional groups present in the molecules. Draw the expected products for the following reaction .
Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev’s rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak…