Week_2_PurpleBook2007

Week_2_PurpleBook2007 - 32 Alkenes: Isomers and...

Info iconThis preview shows pages 1–7. Sign up to view the full content.

View Full Document Right Arrow Icon
Alkenes: Isomers and Nomenclature 1. There are 6 unique alkene isomers of the hydrocarbon C 5 H 10 . Draw each of these isomers, and provide a systematic name for each. 3. Provide a systematic name for the following alkene. 2. For the three alkenes above which are various isomers of pentene, rank them in order of stability. Explain your ranking. Week 2 32
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Carbocation Formation and Rearrangement 1. Each of the following alkenes will generate a carbocation by protonation. Draw a curved arrow mechanism for the single step of carbocation formation, and show the carbocation product. 2. Each of the following alkenes will generate a carbocation by protonation. That carbocation can then rearrange to form a more stable carbocation. Show a curved arrow mechanism for the protonation and rearrangement steps. Make sure you understand why the rearrangement takes place! Week 2 33
Background image of page 2
Carbocation Stability 1. Draw the structure of the methyl cation, CH 3 + . Describe the hybridization, geometry, and orbitals in this species. 2. Each of the following carbocations is significantly more stable than the methyl cation. Explain why each of these species is especially stable. You should use both molecular orbital and resonance arguments in your explanations. H 3 C H 2 C CH 2 H 2 CC H 2 H 3 CO 2 3. Rank the above cations in terms of stability. Again, use both MO and resonance arguments to explain the relative order of stability. Week 2 34
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Alkene Addition Mechanisms Cl 1. Provide a complete curved-arrow mechanism for the following alkene additions. Cl Br HCl HBr Week 2 35
Background image of page 4
Alkene Additions: Application of Polarity 1. a) The reagent I–Cl (iodine chloride) behaves much like the halogens you are familiar with, such as Br 2 and Cl 2 . One thing that makes I–Cl different, however, is that it is polar . On the following structure, show which end of I–Cl has a partial positive charge ( δ + ) and which end has a partial negative charge ( δ ). IC l b) Iodine chloride will add to alkenes via the same mechanism used for Br 2 addition. Predict the product that would result from the following alkene addition, and provide a complete curved-arrow mechanism for this alkene addition. I–Cl structure of product: Week 2 36
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon