Draw structural formulas for the alkoxide ion and the alkyl(aryl)bromide that may be used in a Williamson synthesis of the ether shown. -CH2- • You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na", I', in your answer. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu.

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

Question #9

Draw structural formulas for an aldehyde or ketone and alkyl (or aryl) bromide that could be used in a Grignard synthesis of the alcohol shown. CH3 CH3CH2CCH2CH3 ОН • You do not have to consider stereochemistry. • If there is more than one combination, draw only one. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu.

Draw structural formulas for the alkoxide ion and the alkyl(aryl)bromide that may be used in a Williamson synthesis of the ether shown. ● ● You do not have to consider stereochemistry. Do not include counter-ions, e.g., Na+, I', in your answer. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ← -CH₂- 8 ChemDoodle Ⓡ ۵۰ #[ ] در

Draw structural formulas for the alkoxide ion and the alkyl(aryl)bromide that may be used in a Williamson synthesis of the ether shown. CH3 CH3CH₂-O-CCH₂CH3 CH3 You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na*, I, in your answer. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right **** corner. Separate structures with + signs from the drop-down menu. /n [F

Draw structural formulas for an aldehyde or ketone and alkyl (or aryl) bromide that could be used in a Grignard synthesis of the alcohol shown. CH3ČCH2CH2CH2CH2OH CH3 • You do not have to consider stereochemistry. If there is more than one combination, draw only one. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple reactants using the + sign from the drop-down menu.

5. Homework Help

Draw structural formulas for an aldehyde or ketone and alkyl (or aryl) bromide that could be used in a Grignard synthesis of the alcohol shown. H3C. H3C1 -CH₂OH . You do not have to consider stereochemistry. If there is more than one combination, draw only one. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. . Separate multiple reactants using the + sign from the drop-down menu. ChemDoodleⓇ Sn [F

Draw structural formulas for the alkoxide ion and the alkyl(aryl)bromide that may be used in a Williamson synthesis of the ether shown. ● H3C Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Do not include counter-ions, e.g., Na+, I-, in your answer. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● 10-CH₂CH₂CH3