Alcohols and Phenols Questions and Answers

O N S Ph OH SnC14 CI 12 NaHCO3 PhCH NH

In order to effect the transformation shown the reagents needed are CH3 CH3 OH OH Cat Os04 TMANO acetone H20 AgOAc 12 H2O ACOH Cat K20s2 OH 4 DHQD 2PHAL CINANTS t BuOH H20 TiO i Pr 4 t BuOOH DET

What is the steveochemical relationship between the following compounds OH They are enantiomers HO 11 They are identical not isomers They are different conformations of the same compound They are constitutional isomers They are diastereomers

Predict the major product for the following reaction OI Oll OIV H OH 1 TsCl pyridine 2 Nal CH3 Ill CH3 H 11 H OTS CH3 H H CH3 H I IV H Ts CH

Predict the major product of the following reaction CH8 A LOH O A O O B C D H H O OH B C OH D OH E OH OH

The energy diagram depicts the substitution reaction shown below Select the correct structure of intermediate III CH7 Free Energy O O OH CH OH H OH J Reaction Coordinate H CO

Which two patterns of arrow pushing are seen in this reaction CH6 Br OH O Proton transfer and loss of a leaving group O Loss of a leaving group and nucleophilic attack Nucleophilic attack and rearrangement Rearrangement and proton transfer

13 How would you accomplish the following conversion OH OH 8 points

12 7 Identify the reagents that you would use to accomplish each of the following transformations OH you Br OH b Br OH OH 60 d c

2 45 Predict the products for each of the following 1 0 2 DMS J 1 0 21 DVS 3 Excess LIAIH 4 1 0 b 3 Excess LIAIH 4 H 0

CHUCH MOCI 2 1 0 a CH CH CH OH CH b CH CH OH c CH CH CH OH d CH CH CH CH OH OB

COA OB OD OE d A P P 8 Lindler s catalyst C MESO M SO D RAPO NaOH E Na Ma

This is an example of a CH OC CH 14CH3 CHOC CH 14CH3 H OPOCH CH NH wax O glycerophospholipid steroid O fatty acid Otriacylglycerol

catalytic acid in water O Option 1 of et upon hydrolysis with g O Option 2

Which 2 step process would convert the reactant to the product Excess reagent is implied if needed Hint Attempt this question towards the end of the exam so flag it if you get it in the beginning t BUOK 1 TsCl py OH 1 excess NaNH2 2 water 2 OsO4 Na2SO3 conc sulfuric acid dilute sulfuric acid OH HBr ROOR NaOEt HBr

Which 3 step process would convert the reactant to the product Excess reagent is implied if needed Hint Attempt this question towards the end of the exam so flag it if you get it in the beginning OH 1 1 BH3 THF 2 H2O2 NaOH 1 Hg OAc 2 aq 2 NaBH4 Br2 2 x KMnO4 NaOH dilute sulfuric acid HBr ROOR OH 3 HBr t BUOK TsCl py

What series of synthetic steps could be used to carry out the transformation shown below A Na2Cr207 H2SO4 B LiAlH4 C PCC D BH3 H2O2 OH step 1 Select step 2 Select CHO

Pick reactants DA OB DC Br 2 2 B NaH OH La OH D E

Predict major product OA OH 0000 OB OC OD OH OH PBry B OH D OH

What is the major product of the reaction shown below CH3 OA OB CH3 OC O A OH OH Ono reaction NaOCI CH3 B H HO CH3 C

Transmittance 80 75 Rolando 4 22 22 120 CYCLOHEXANOL 100 80 60 40 20 4000 3800 2800 3000 3200 3400 3600 2600 prasm per th 2200 2000 Wavenumbers cm 1 2400 1800 1000 1200 1400 1600 800 600

Classify the reaction below as an LOH O reduction O oxidation O neither O

Which of the following alcohols will have a product with Na Cr O7 H SO4 tert butanol O cyclohexanol Opentan 3 ol O both A and B both B and C

When CH3CCI is treated with excess phenylmagnesium bromide in ether, with subsequent aqueous work up, the resultant product: can undergo elimination with Kotbu can be oxidized by jones reagent can be reduced with Lithium aluminum hydride can undergo SN2 reaction to produce alkyl halide

True / False: An alcohol is an organic compound that contains the hydroxyl group True False

Provide a sequence of laboratory reactions which could be used to prepare 2-methylpropylmagnesium bromide [whose formula is (CH₂)2CHCH₂MgBr] starting with 2-methylpropene. Your sequence must proceed through an alcohol as an intermediate product.

Choose the correct product for the following reaction: 2-bromo-2-methylpropane no reaction 2-bromopropane 2-methyl-2-propanol 2-bromopropanol

Which of the following statements is true? Multiple Choice Saliva contains keratin, a slippery protein that is used to make mucus. Insulin and glucagon are proteins. Most human cells rely almost entirely on protein for energy. Edema occurs when a healthy person consumes more protein than needed.

Read the following lines from Chapter 2 of Oliver Twist by Charles Dickens. 'Please, sir, I want some more.' The master was a fat, healthy man; but he turned very pale. He gazed in stupefied astonishment on the small rebel for some seconds, and then clung for support to the copper. The assistants were paralysed with wonder; the boys with fear. 'What!' said the master at length, in a faint voice. What do you understand about the situation from the dialogue? Ecstatic Shocking and Tense Calm

Calculate the percentage composition for SiO2. Mass percentage of silicon = ____% Mass percentage of oxygen =____%

During acid-catalyzed hydration, which of the following alkenes might lead to a rearranged product? 2-methylbut-2-ene 3,3-dimethylbut-1-ene 4-methylpent-1-ene 3-methybut-1-ene Both 3,3-dimethylbut-1-ene and 3-methybut-1-ene All undergone carbocation rearrangement.

Wine goes bad soon after opening because the ethanol (CH₂CH₂OH) dissolved in it reacts with oxygen (O₂) gas to form water and aqueous acetic acid (CH3COOH), the main ingredient in vinegar. Calculate the moles of acetic acid produced by the reaction of 0.10 mol of ethanol. Be sure your answer has a unit symbol, if necessary, and round it to the correct number of significant digits.

Which compound is an alcohol? (A) butanal (B) butanone (C) butane (D) 2,2-butandiol

Water is capable of dissolving a variety of different substances, which is why it is such a good solvent. It is often called the universal solvent because it dissolves more substances than any other liquid. The reason for this is best explain by which of these? Select one: a. Water is polar with a positive and negative side. b. Water bonds with most chemicals. c. Water expands as it freezes. d. Water is the most abundant liquid on earth.

A student conducts an experiment to determine the specific heat of iron. The student calculated the specific heat to be 0.40 J/g°C. The actual value is 0.45 J/g°C. Calculate the percent error. SHOW ALL WORK

How many of the following alcohols give turbidity immediately with Lucas reagent? Cyclopropylmethanol, benzyl alcohol, t-butyl alcohol, isopropyl alcohol, sec- butyl alcohol, neopentyl alcohol, but-3-en-2-ol

There are 12 eggs in a dozen. If a farmer's chickens produce an average of 322 dozen eggs in a month, how many eggs are reported per month? 322 dozen x 12 eggs/dozen eggs

Considering your properly drawn Lewis dot structure and what you know about polarity and "like dissolves like", select all of the compounds that are miscible with ethanol, CH3CH2OH. A. HF B. CH4 C. CH3OH (methanol) D. S02 E. CH20 F. C6H6 G. N2 H. Al2O3 I. NH3 J. CO2

MultiStep Synthesis Over the next 3 weeks, you will be conducting your own multi-step synthesis. You will be provided with cyclohexanol and all the reagents needed to make 1-butylcyclohexene. Part 1: plan your synthesis The order in which you conduct your reaction steps in incredibly important. Please devise your plan, send it to me and then come to lab ready to conduct the first reaction on week 1 (wednesday 02/16). Once your plan is approved, I will provide you with the experimental details for each step.

The bond-line structure of the compound has a SMILES string of CCCC(=O)CCC. The conversion of 1-butanol to the given compound can be performed with some combination of the reagents listed below. Give the necessary reagents 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. 1) CH3CH₂MgBr; 2) H3O+ B. conc. H₂SO4, heat C. H₂, Lindlar's cat. D. DMP or PCC E. 1) CH3CH₂CH₂MgBr; 2) H3O+ F. Na₂Cr₂O7, H₂SO4, H₂O

What carbonyl compounds might you start with in a Grignard synthesis of the following 1-ethylcyclohexanol

Ethers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of 1-iodo-2-methylpropane with the following ● + • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading. Do not include counter-ions, e.g., Na, I, in your answer. ● 0 Na

O QH 0 H₂O+ OH Product can give positive test with :- → Product 2, 4 DNP, FeCl3, Cerric ammonium nitrate and NaHCO3 2, 4 DNP, FeCl3, NaOH and NaHCO3 FeCl3, Cerric ammonium nitrate, Tollen's reagent and NaHCO3 FeCl3, Cerric ammonium nitrate, NaOH and NaHCO3