6. Pick one from a) to g), one from h) to m) and any other one of the following compounds (three compounds altogether), and provide a synthetic scheme to produce the following compounds starting from toluene and/or methylcyclohexane, using any inorganic material, and any organic material with 4 carbons or less. Reagents that are not included in the final product maybe used regardless of the number of carbon atoms (for example, you may use PPh3 to perform a Wittig reaction). If you have produced a compound, you can use that compound in subsequent work without showing its synthesis again. a) b) CH3 d) CH3 gula g) HO h) H₂C H₂C CH₂ HO CH₂ H₂C CH3 CH3 CH3 CH₂ i) HO НО. m) CH3 j) NH CH3 CH3 H₂C. CH3 k) H₂C_ CH3 Br OH CH3 CH3

Draw compound A and B and identify reagents 1,2 and 3

Curved arrows are used to illustrate the flow of electrons. Using the provided starting structure, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. Then draw any missing organic intermediates or products for this reaction. Include all lone pairs in the structures. Ignore inorganic byproducts and counterions. H 0:0- HsC H Select to Add Arrows H HaC Select to Add Arrows CH₂OH, H CH3OH, H* CH3OH, H* HaC H Select to Add Arrows 1 CH3OH, H+ HaC H H Select to Add Arrows I

4. Synthesis Using the carbon-containing starting material(s), propose a synthesis by drawing structures for all intermediates. The carbon atoms in the product must originate from the starting material(s) (or a carbene/carbenoid or CO2), but you may use as many equivalents of each starting material as you would like, and any reagent/reaction you know. (note: no mechanisms are required). OH

HW 11#17

Orgo question

Chemistry

Just the second reaction. Please show in between steps and not just the product.

Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic steps. Be sure to account for all bond-breaking and bond-making steps. 1 I I :O: H Select to Add Arrows ether EN: CH2N2 :O: NEN: Problem 13 of 20 Please select a drawing or reagent from the question area Submit

Write the structural formula of the organic product for the given reaction between an alkyne and an alkyl halide. The alkyne group is shown and should be entered as "CC" without the triple bond. Enter CC before associated HH atoms (e.g., CH3CH2CH2OCHCHCH3).                      1.NaNH2 CH3CH2CCH------>                     2. CH3CH2b2