4. Grignard reagents are powerful nucleophiles that will react with a variety of electrophiles such as alkyl halides but ALSO act as strong bases, especially when they are sterically hindered. What would be the MAJOR organic product of the reaction below? Show a curved arrow mechanism for this transformation and give a mechanism type/name (E1, E2, SN1, SN2, 1,2-addition or nucleophilic acyl substitution). +MgBr tor -Br 1. 2. H₂O*

2. Draw the mechanism using curved arrows and predict the product(s) of the following reaction below. Your answer should also include any stereochemistry if applicable. H30 ?

Write out the mechanism (intermediate/transition state) for this reaction; NaOCH, Ę₂ CH3 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 cyclohexanone (reagent, product). b) Write out 3 preparations of 2-butanol, 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 4-phenylbutanoic 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.

R Please don't provide the handwriting solution

2. In each synthesis, either the reagents or products are missing. Fill in the missing reagents or product. If there is more than one product, show only the major one. Show stereochemistry where appropriate. (a) (b) H₂N. OH + (c) H₂N ZEC- (d) OPP + OPP (e)

Continue the synthesis by selecting the reagents necessary for the next transformation shown. ? Br The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B C EtONa HBr, ROOR H₂, Lindlar's cat. D E F HBr HC=CNa H₂, Pd G H I 1) 03; 2) DMS 1) NaNH2; 2) EtBr 1) R₂BH; 2) H₂O2, NaOH

Given your analysis of the starting material in parts 1 and 2, order the synthetic steps required to bring about this transformation successfully in the correct order. The steps of the reaction scheme are shown below. Step 1 Step 2 Step 3 Br X- Reagents (6 items) (Drag and drop into the appropriate area below) Steps Step 1 NaBH4, CH3OH Mg(s), dry diethyl ether No more items Step 2 Step 3 CH3Li, THF, - 78°C KCN, ethanol HOCH2CH2OH, H+ i) LiAlH, THF ii) H3O+ iii) OH-

Please show the products of following reactions and reaction mechanisms for each using the right arrows and define it as Sn2, Sn1, E2 or E1.Explain why do you choose that product and mechanism or in case something else happens explain why.

I'm confused on questions 2, 5, and 6. Solve at least question 2

XVI. Provide the mechanism for the following synthetic transformation. 1. CH3CH₂CH₂CH₂Li (2 equivalents) 2. H₂C=O 3. H¹, H₂O ỌCH3 F OCH3 & CH₂. OH CH,CH,CH,CH3