Alcohols and Phenols Questions and Answers

4 What is the product of the following reaction OH 1 NaH 2 propyl iodide A B C D O

What is are the major substitution products for the following reaction A B C E Product 1 is major H3CO Product 2 is major D A mixture of 1 and 5 would be major A 1 1 mixture of 2 and 3 would be major A mixture of 4 and 5 would be major OH OCH3 conc H SO4 CH3OH OCH3 Product s OH HO

Which of these is inaccurate CI DIBAIH DMSO 0 THF Zn HCI AICI OCHS 1 CH Br Mg ether 2 H O H CH

11 15 Propose an efficient synthesis for each of the following transformations a b OH OH y

Draw the alcohol needed to produce the alkyl chloride under the conditions shown Draw Alcohol Reactant CI SOCI2 pyridine

Which alcohol would undergo a dehydration reaction the fastest when treated with concentrated H2SO4 A A B B C C D D E E OH OH B OH OH LL F OH

Give the major product in each of the following HO CH3 H3C CH3 CH3 H SO4 dehydration

True False The following compound is phenol OH O True O False

A OA OB Pick the Grignard reagent and an epoxide to make this alcohol OC OD MgBr B MgBr C OH X D

Draw the product of this reaction Ignore inorganic byproducts Br2 2 equiv Select to Draw I I I I I I I I I I

Mechanisms Provide a complete stepwise mechanism to explain each of the following transformations Be certain to include ALL intermediate structures and electron shift arrows that clearly indicate the electron transitions and bond changes that convert one structure to the next a b Br HO OH H O EtOAc H SO4 H O at

The synthesis above can be performed with some combination of the reagents listed below Give the necessary reagents in the corre order without any added commas or spaces between the letters Be sure to consider stereochemistry and regiochemistry A 03 B DMS C H O D Br2 CCl4 E NaNH2 F H Pd BaSO4 quinoline G H Ni H CH3 OTS I TsCl py J CH3CH Br

How many hydrogen atoms are present in the following compound a 10 O b 9 Oc 11 d 12 OH

the final product 10 What Is 2 3 dimethyl pentam 1 01 w Nay Cr 07 1 50 4 methanol CH3OH in acid name product

1 12 pts Provide the structure s of the expected major organic product s Unless mentioned otherwise you can assume that all reagents are present in one mole Show stereochemistry where needed and write NR if there is no reaction non hindered Base NaOC H5 C H5OH aifsev a O H Br b HC C CH3 heat nun hind 1 CH Li THF 2 3 HO C Hs

Which set of reagents would be suitable for the completion of the following flow chart OH xx A PCC B H CRO4 THF 2 NaOH H O2 OH C 1 Hg OAC 2 H O 2 NaBH4 OI H II C III G IV J V B OI E II D III A IV J V A IV E H3PO4 heat F KOtbu G 1 LiAlH4 2 H3O H 1 NaBH4 2 H3O J 1 Ph MgBr ether 2 H3O I F II D III B IV J V A OH I F II D III A IV J V B D 1 BH3