6A1: Distinguish between synthetic and retrosynthetic transformations to solve problems and predict starting materials and products. Draw any retrosynthetic sequence where a hydroxyl cycloalkane retron can be retrosynthesized into an appropriate cycloalkene, where the cycloalkene can be retrosynthesized into an appropriate cycloalkane halide. While you are allowed to work out this problem synthetically, you MUST report your final response in the retrosynthetic direction using the symbology we learned in lecture/

Draw a step-by-step mechanism for the transformation shown below (no additional reagents are needed), showing all electron flow with arrows.

or the following carbocation determine if it is likely to rearrange, and if so, select the correct carbocation rearrangement: о ЊС Н.С O CH₂ CH₂ O There is no rearrangement for this carbocation. О HỌC CH НС H₂C сх-сно H HỌC CH X _CH2 HỌC HỌC y J Н CH₂ зорил CH₂ НС- - H.C H.C CH 3 -C+ Н.С ЊС CH₂ CH₂ CH CH₂ CH CH₂ CH₂

The following reaction is similar to the dehydration of 2-methylcyclohexanol. However, a significant amount of a tetrasubstituted alkene is expected. Predict the structure for this tetrasubstituted alkene. Also, using curved arrows, provide a reasonable mechanism for its formation. Но. H3PO4 ??? A (-H2O)

Which of the following reagents is best to achieve the given transformation? H₂C 0=s=0 0000 → KOtBu OCH3OH NaOH TsCI, Py

Predict the major products of this reaction. ХХ Cl₂ hv ? Draw only the major product or products in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. If there will be no products because there will be no significant reaction, just check the box under the drawing area and leave it blank. Note for advanced students: you can ignore any products of repeated addition. Click and drag to start drawing a structure. E 'n X 0:0 to

When the following alkene A was treated with sulfuric acid in water, the cyclohexanol product B was formed. Using curved arrows give the mechanism for this reaction, including any regioselectivity or stereoselectivity. CH3 CH3 OH H2SO4 CH3 A H₂O CH3 ៣ B

Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. CH3 CH3 H3PO4 HO, + H3C CH3 HO HO First stage in synthesis of the epoxy and polycarbonate ingredient bisphenol-A You do not have to consider stereochemistry. Include all valence lone pairs in your answer. In cases where there is more than one answer, just draw one.

Complete the following reactions by providing the missing product(s). Determine what mechanism operates in each case (SN1, SN2, E1, or E2). Show the stereochemistry of the product(s) where appropriate. If more than one product is formed circle the major one.

Fill in the major products to complete the transformations. Be sure to pay carefulattention to stereochemistry where appropriate. If the major product is a pair of enantiomers or diastereomers be sure to draw them both. And indicate whether you have drawn an enantiomer or a diastereomer. (Don't forget about rearrangement).