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- Which of the following carbocations would be expected to rearrange? None of these would be expected to rearrange. „CH3 CH;CCH,CH3 ČH3 .CH3 „CH3+ 1. Draw line structures of all of the C3H17* carbocations that have the carbon skeleton shown below. 2. Circle the most stable carbocation of those that you have drawn.2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: CN 1) NaCN 2) H+ OH 1) NaBH4 2) H3O+ OH Group -H -CN A Value (kcal/mol) Defined as 0 0.2 kcal/mol -OH 1.0 kcal/mol c. For any products that do have the most stable conformation, does our understanding of the mechanism allow for ‘thermodynamic control'? d. If one of the products is not the most stable, can you explain the observed product based on ‘kinetic control'? (Does the most easily formed transition state result in the observed product?) Consider the chair-like conformation of the starting material.
- 2) Rank the following carbocations in order of stability. 1-most stable CH₂ CH CH*We'll see in the next chapter that the stability of carbocations depends on the number of alkyl substituents attached to the positively charged carbon - the more alkyl substituents there are, the more stable the cation. Which of the two carbocations in each pair is more stable? If they are of equal stablility, specify this. a) b) H3C + CH3 gron CH3 -CH3 H₂C b -CH3 CH3 CH3Arrange the following alkenes in their correct order of stability. 1=Most stable and 4=least stable.
- b Assuming that halogens add to alkynes in the same manner that they add to alkenes, write a mechanism for the reaction step below. Use curved arrows to show electron reorganization. Arrow-pushing Instructions H3C C↔X ™ Br: CH3 BrZaitsev's rule can be used to predict the major alkene product in a dehydration reaction. What is the name of the major product of the dehydration reaction shown below? CH3 CH3CHCH₂CHCH3 ОН 4-methyl-1-pentanol 4-methyl-4-pentene O2-methyl-2-pentanol 4-methyl-2-pentene H heatDraw a line-angle formula for the major organic product of the following SN2 reaction. acetone CH;CH2CH2CI Na* CN + Where configuration of the starting material is given, show the configuration of the product. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it. • In cases where there is more than one answer, just draw one. P орy aste ChemDoodle
- Which of the following alkenes releases the least heat per mole upon hydrogenation? O 2-methyl-2-butene O 1-methylcyclobutene O (Z)-2-pentene 1-pentene O (E)-2-penteneRank the following carbocations in order of increasing amounts of hyperconjugation. The first in your list should have the least amount. 1 3 01<2<3 O2<1<3 O2<3<1 3 2< 1 O1<3<2 2.Name (including E/Z stereochemistry) the five alkenes that can produce 3-bromo-3-methylhexane on reaction with HBr. Draw the skeletal structure of each molecule.
