CH3 CH3 Br Br2 CH3 CH2CI2 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 ig:

CH3 CH3 Br Br2 CH3 CH2CI2 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 ig:

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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196. Subject : - Chemistry
Ph3P-CHCH3 H₂C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. CH3 00 + The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an SN2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene X m CH3 The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C=C bond is precisely where the C=O bond was in the reactant and no isomers (other than E/Z isomers)…
Draw the structure of the four allylic halides formed when 3-methylcyclohexene undergoes allylic halogenation with NBS + hv.
This alkyl halide can be prepared by electrophilic addition of HBr to 2 different alkenes. Draw them.
The SN1 mechanism starts with the rate-determining step which is the dissociation of the alkyl halide into a carbocation and a halide ion. The next step is the rapid reaction of the carbocation intermediate with the nucleophile; this step completes the nucleophilic substitution stage. The step that follows the nucleophilic substitution is a fast acid-base reaction. The nucleophile now acts as a base to remove the proton from the oxonium ion from the previous step, to give the observed product. Draw a curved arrow mechanism for the reaction, adding steps as necessary. Be sure to include all nonzero formal charges.
9.
Draw a structural formula for the major organic product of each reaction and specify the most likely mechanism by which each is formed.
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).
Suppose you were told that each reaction is a substitution reaction, but you were not told the mechanism. Describe how you could conclude from the structure of the haloalkane or cycloalkene, the nucleophile, and the solvent that each reaction is an SN1 reaction.
Suppose you are told that each reaction is a substitution reaction but are not told the mechanism. Describe how you could conclude from the structure of the haloalkane, the nucleophile, and the solvent that each reaction is an SN2 reaction.
1,3- Butadiene undergoes an electrophilic addition with Hbr. Complete the steps in the mechanism to produce the product.
10) Synthesis: Make the following products from a suitable cyclic alkene starting material. Look at the functional group PATTERN present in the molecule, including stereochemistry. Br CH3 Br CH3