Exam 8: Alcohols, Phenols, Ethers, and Their Sulfur Analogs

Instructions: Provide correct IUPAC names for each of the structures below. Name:

Instructions: Provide correct IUPAC names for each of the structures below. Name:

Instructions: To answer the following question(s), consider the reaction below. Refer to instructions. Provide the IUPAC name for the product alcohol.

Choose the best reagent for carrying out the following reactions from the list below. Place the letter of the reagent(s) in the box over the reaction arrow. Only one letter per box. A. $\quad m-\mathrm{ClC}_{6} \mathrm{H}_{4} \mathrm{CO}_{3} \mathrm{H} ~~~~~~~~~~~~~~~~~$ B. $\quad \mathrm{H}_{2} / \mathrm{Pd}$ C. $~~~~$ warm $\mathrm{H}_{2} \mathrm{SO}_{4} / \mathrm{H}_{2} \mathrm{O} ~~~~~~~~~~~~~~~~~~~~$ D. $\mathrm{PCC}, \mathrm{CH}_{2} \mathrm{Cl}_2$ $\mathrm{E.} \quad \mathrm{LiAlH}$ in ether then $\mathrm{H}_{3}O^+ ~~~~~~~~~~~~~~~~~$ F $\quad \mathrm{NaOH}$ heat

Instructions: Refer to the data below to answer the following question(s). $\mathrm{p} K_{\mathrm{a}} \mathrm{s}$ of Some Phenols $~~~~~~~~~~~~~~~~~~~~\frac{\underline{Y}}{-\mathrm{H}} \quad~~~~~~ \frac{\mathrm{p} K_{\mathrm{a}}}{9.89}$ m- 8.28 p- 7.17 m- 9.65 p- 10.21 Refer to instructions. a) The weakest acid in the table is b) Which of the acids in the table has the weakest conjugate base?

Instructions: Consider the reaction below to answer the following question. Refer to instructions. Mechanistically, the Williamson ether synthesis outlined above is:

Instructions: Provide correct IUPAC names for each of the structures below. Name:

Instructions: To answer the following question(s), consider the reaction below. Refer to instructions. On the templates provided below, draw both conformations of the alcohol product. Circle the least stable conformation.

Instructions: Draw structures corresponding to each of the following IUPAC names. Draw: cyclopropyl ethyl sulfide

Instructions: Draw structures corresponding to each of the following IUPAC names. Draw: Dicyclohexyl sulfide

Instructions: Choose the best reagent(s) for carrying out the following conversions from the list provided below. Place the letter of the best choice in the blank. Reagents may be used more than once. $a.~~~~~ \mathrm{CrO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4}, \mathrm{H}_{2} \mathrm{O}$ $b.~~~~~$ 1. $\mathrm{NaBH}_{4}$ , ethanol $~~~~~~~~$ 2. $\mathrm{H}_{3} \mathrm{O}$ $c.~~~~~$ 1. $\mathrm{LiA1}_{4}$ , ether $~~~~~~~~$ 2. $\mathrm{H}_{3} \mathrm{O}^{+}$ $d.~~~~~~$ periodinane Refer to instructions. _____

Instructions: To answer the following question(s), consider the reaction below. Refer to instructions. The alcohol product is classified as a:

Instructions: Choose the best reagent(s) for carrying out the following conversions from the list provided below. Place the letter of the best choice in the blank. Reagents may be used more than once. $a.~~~~~ \mathrm{CrO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4}, \mathrm{H}_{2} \mathrm{O}$ $b.~~~~~$ 1. $\mathrm{NaBH}_{4}$ , ethanol $~~~~~~~~$ 2. $\mathrm{H}_{3} \mathrm{O}$ $c.~~~~~$ 1. $\mathrm{LiA1}_{4}$ , ether $~~~~~~~~$ 2. $\mathrm{H}_{3} \mathrm{O}^{+}$ $d.~~~~~~$ periodinane Refer to instructions. _____

Instructions: Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry. Write the product(s):

Answer the following questions. a) Which of the following would produce an aldehyde when reacted with periodinane? a. only 1 b. only 3 c. only 1 and 3 d. only 2 and 3 b) If $\mathrm { CrO } _ { 3 }$ were used in place of periodinane, how would the product of the reaction differ? a. a ketone would be produced b. a carboxylic acid would be produced. c. a mixture of aldehyde and ketone would be produced d. the reaction product would be the same in both cases

Which of the following are ethers?

A useful and general method for the synthesis of alcohols is the addition of Grignard reagents to carbonyl compounds. Show what Grignard reagent and what carbonyl compound you would start with to prepare each alcohol below. List all possibilities.

Instructions: Draw structures corresponding to each of the following IUPAC names. Draw: 2-phenylpropan-2-ol

Instructions: Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry. Write the product(s):