11. For the following use ONLY reactions we have studied in class. Check your notes or the Powerpoint slides for preparations and reactions of relevant functional groups. a) Write out 6 completely different reactions of cyclopentanone (reagent, product). b) Write out 3 preparations of 1-phenylethanol, using a different starting material for each one. You may use preps where you just change the functional group, and/or preps where you construct the carbon chain. c) Write out 3 preparations of 2-phenylacetic acid, a different starting material for each one. You may use preps where you just change the functional group, and/or preps where you construct the carbon chain.

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.

B part

2. Starting from 1-propyne as your sole carbon source for the product, provide the steps required (either above the reaction arrow, or show your work below) to perform this reaction. You can use any chemical transformation we have discussed in lecture, but only the carbons from the starting material can be used for carbons of the product. If any steps employ a S¹, S², E2, or E1 label as such. HO

For #9. use ONLY reactions we have studied this semester. 9. a) Write out seven separate reactions of 1-pentene, including reagent(s) and products(s). Include stereochemistry where relevant. b) Write out five separate reactions of 1-pentyne, including reagent(s) and product(s). Include stereochemistry if relevant.

Answer choices are the ones above.

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

You are given the following reactions to complete in lab. However, you recognize an issue with the reaction. 1. Determine why the reactions will not work or why the reactions will give a poor yield? 2. How can you resolve the issues and run the reactions to obtain a better yield? Fix the reactions by redrawing each reaction with the solution (corrected starting materials/reagents/products/etc.).

Make a table like Table 1 below to record the volumes you will use of each reagent in the different trials. This plan is part of your prelab. ble 1. Volumes of reactants for each trial NaHSO3 H₂SO4 Total Trial KIO3 volume H₂O volume Starch volume volume volume Volume 1 1.0 mL 1.0 mL 1.0 mL 1.0 mL 1.0 mL 5.0 mL 2 1.0 mL 5.0 mL 3 1.0 mL 5.0 mL 4 1.0 mL 5.0 mL 1.0 mL 1.0 mL 1.0 mL 5.0 mL 5 1.0 mL 1.0 mL

Can you please help with homework questions. Thank you.