a) Styrene (PhCH=CH2)
Interpretation:
How to prepare styrene from 2-phenylethanol is to be stated.
Concept introduction:
Alcohols undergo dehydration when treated with POCl3 in pyridine to yield
To state:
How to prepare styrene from 2-phenylethanol.
Answer to Problem 47AP
Styrene can be prepared by treating 2-phenylethanol with POCl3 in pyridine.
Explanation of Solution
2-Phenylethanol when treated with POCl3 in pyridine eliminates a molecule of water from the side chain to yield styrene.
Styrene can be prepared by treating 2-phenylethanol with POCl3 in pyridine.
b) Phenylacetaldehyde (PhCH2CHO)
Interpretation:
How to prepare phenylacetaldehyde from 2-phenylethanol is to be stated.
Concept introduction:
Dess-Martin periodinate in dichloromethane oxidizes 10alcohols to
To state:
How to prepare phenylacetaldehyde from 2-phenylethanol
Answer to Problem 47AP
Phenylacetaldehyde can be prepared by oxidizing 2-phenylethanol with Dess-Martin periodinate in dichloromethane.
Explanation of Solution
2-phenylethanol is a 10 alcohol. It gets oxidized to phenylacetaldehyde when treated with Dess-Martin periodinate in dichloromethane.
Phenylacetaldehyde can be prepared by oxidizing 2-phenylethanol with Dess-Martin periodinate in dichloromethane.
c) Phenylacetic acid (PhCH2COOH)
Interpretation:
How to prepare phenylacetic acid from 2-phenylethanol is to be stated.
Concept introduction:
CrO3 in acidic solutions oxidize 10 alcohols directly into acids and 20 alcohols to ketones. It does not oxidize 30 alcohols.
To state:
How to prepare phenylacetic acid from 2-phenylethanol.
Answer to Problem 47AP
Phenylacetic acid can be prepared by oxidizing 2-phenylethanol with CrO3 in acidic solutions.
Explanation of Solution
2-phenylethanol is a 10 alcohol. It gets oxidized to phenylacetic acid when treated with CrO3 in acidic solutions.
Phenylacetic acid can be prepared by oxidizing 2-phenylethanol with CrO3 in acidic solutions.
d) Benzoic acid
Interpretation:
How to prepare benzoic acid from 2-phenylethanol is to be stated.
Concept introduction:
KMnO4 in acidic solutions oxidize
To state:
How to prepare benzoic acid from 2-phenylethanol.
Answer to Problem 47AP
Benzoic acid can be prepared by oxidizing 2-phenylethanol with KMnO4 in acidic solutions.
Explanation of Solution
2-phenylethanol is a 10 alcohol. It gets oxidized to benzoic acid when treated with KMnO4 in acidic solutions.
Benzoic acid can be prepared by oxidizing 2-phenylethanol with KMnO4 in acidic solutions.
e) Ethylbenzene
Interpretation:
How to prepare ethylbenzene from 2-phenylethanol is to be stated.
Concept introduction:
Alcohols undergo dehydration when treated with POCl3 in pyridine to yield an alkene. The alkene upon reduction gives the
To state:
How to prepare ethylbenzene from 2-phenylethanol.
Answer to Problem 47AP
Ethylbenzene can be prepared from 2-phenylethanol by following the steps shown below.
Explanation of Solution
2-Phenylethanol when treated with POCl3 in pyridine eliminates a molecule of water from the side chain to yield styrene. When treated with H2/Pd, the double bond in the side chain gets reduced to yield ethyl benzene.
Ethylbenzene can be prepared from 2-phenylethanol by following the steps shown below.
f) benzaldehyde
Interpretation:
How to prepare benzaldehyde from 2-phenylethanol is to be stated.
Concept introduction:
Alcohols undergo dehydration when treated with POCl3 in pyridine to yield an alkene. The alkene upon ozonolyzis followed by reduction will yield the aldehyde required.
To state:
How to prepare benzaldehyde from 2-phenylethanol.
Answer to Problem 47AP
Benzaldehyde can be prepared from 2-phenylethanol by following the steps shown below.
Explanation of Solution
2-Phenylethanol when treated with POCl3 in pyridine eliminates a molecule of water from the side chain to yield styrene. When styrene is subjected to ozonolysis followed by reduction, the double bond in side chain gets cleaved resulting in the formation of benzaldehyde.
Benzaldehyde can be prepared from 2-phenylethanol by following the steps shown below.
g) 1-phenylethanol
Interpretation:
How to prepare 1-phenylethanol from 2-phenylethanol is to be stated.
Concept introduction:
Alcohols undergo dehydration when treated with POCl3 in pyridine to yield an alkene. The alkene adds a molecule of water following oxymercuration-demercuration process. The addition will take place following Markovnikov regiochemistry.
To state:
How to prepare 1-phenylethanol from 2-phenylethanol.
Answer to Problem 47AP
1- Phenylethanol can be prepared from 2-phenylethanol by following the steps shown below.
Explanation of Solution
2-Phenylethanol, when treated with POCl3 in pyridine eliminates a molecule of water from the side chain to yield styrene. When styrene is subjected oxymercuration-demercuration processes, a molecule of water is added, following Markovnikov regiochemistry, to the double bond. The –OH adds on to the more alkyl substituted carbon and H to the less alkyl substituted carbon in double bond to yield 1-phenylethanol.
1-Phenylethanol can be prepared from 2-phenylethanol by following the steps shown below.
h) 1-Bromo-2-phenylethane
Interpretation:
How to prepare 1-bromo-2-phenylethane from 2-phenylethanol is to be stated.
Concept introduction:
Alcohols yield the corresponding alkyl bromides when treated with PBr3.
To state:
How to prepare 1-bromo-2-phenylethane from 2-phenylethanol is to be stated.
Answer to Problem 47AP
1-Bromo-2-phenylethane can be prepared from 2-phenylethanol by following the steps shown below.
Explanation of Solution
When 2-phenylethanol is treated with PBr3, a bimolecular nucleophilic substitution of –OH by Br takes place to yield 1-bromo-2-phenylethane.
1-Bromo-2-phenylethane can be prepared from 2-phenylethanol by following the steps shown below.
Want to see more full solutions like this?
Chapter 17 Solutions
Organic Chemistry
- a) A favorable entropy change occurs when ΔS is positive. Does the order of the system increase or decrease when ΔS is positive? (b) A favorable enthalpy change occurs when ΔH is negative. Does the system absorb heat or give off heat when ΔH is negative? (c) Write the relation between ΔG, ΔH, and ΔS. Use the results of parts (a) and (b) to state whether ΔG must be positive or negative for a spontaneous change. For the reaction, ΔG is 59.0 kJ/mol at 298.15 K. Find the value of K for the reaction.arrow_forwardA sample of hydrated magnesium sulfate (MgSO4⋅xH2O) is analyzed using thermogravimetric analysis (TGA). The sample weighs 2.50 g initially and is heated in a controlled atmosphere. As the temperature increases, the water of hydration is released in two stages: (a) The first mass loss of 0.72 g occurs at 150°C, corresponding to the loss of a certain number of water molecules. (b) The second mass loss of 0.90 g occurs at 250°C, corresponding to the loss of the remaining water molecules. The residue is identified as anhydrous magnesium sulfate (MgSO4) Questions: (i) Determine the value of x (the total number of water molecules in MgSO4⋅xH2O) (ii) Calculate the percentage of water in the original sample. Write down the applications of TGA.arrow_forwardThe solubility product of iron(III) hydroxide (Fe(OH)3) is 6.3×10−38. If 50 mL of a 0.001 M FeCl3 solution is mixed with 50 mL of a 0.005 M NaOH solution, will Fe(OH)3 precipitate? Show all step-by-step calculations. To evaluate the equilibrium constant, we must express concentrations of solutes in mol/L, gases in bars, and omit solids, liquids, and solvents. Explain why.arrow_forward
- Predict the major products of this organic reaction.arrow_forward2. Provide the structure of the major organic product in the following reaction. Pay particular attention to the regio- and stereochemistry of your product. H3CO + H CN Aarrow_forwardPredict the major products of the following organic reaction.arrow_forward
- 1) The isoamyl acetate report requires eight paragraphs - four for comparison of isoamyl alcohol and isoamyl acetate (one paragraph each devoted to MS, HNMR, CNMR and IR) and four for comparison of acetic acid and isoamyl acetate ((one paragraph each devoted to MS, HNMR, CNMR and IR. 2) For MS, the differing masses of molecular ions are a popular starting point. Including a unique fragmentation is important, too. 3) For HNMR, CNMR and IR state the peaks that are different and what makes them different (usually the presence or absence of certain groups). See if you can find two differences (in each set of IR, HNMR and CNMR spectra) due to the presence or absence of a functional group. Include peak locations. Alternatively, you can state a shift of a peak due to a change near a given functional group. Including peak locations for shifted peaks, as well as what these peaks are due to. Ideally, your focus should be on not just identifying the differences but explaining them in terms of…arrow_forwardWhat steps might you take to produce the following product from the given starting material? CI Br Он до NH2 NH2arrow_forward1) The isoamyl acetate report requires eight paragraphs - four for comparison of isoamyl alcohol and isoamyl acetate (one paragraph each devoted to MS, HNMR, CNMR and IR) and four for comparison of acetic acid and isoamyl acetate ((one paragraph each devoted to MS, HNMR, CNMR and IR. 2) For MS, the differing masses of molecular ions are a popular starting point. Including a unique fragmentation is important, too. 3) For HNMR, CNMR and IR state the peaks that are different and what makes them different (usually the presence or absence of certain groups). See if you can find two differences (in each set of IR, HNMR and CNMR spectra) due to the presence or absence of a functional group. Include peak locations. Alternatively, you can state a shift of a peak due to a change near a given functional group. Including peak locations for shifted peaks, as well as what these peaks are due to. Ideally, your focus should be on not just identifying the differences but explaining them in terms of…arrow_forward
- №3 Fill in the below boxes. HN 1. LAH 2. H3O+ NH2arrow_forwardFor the photochemical halogenation reaction below, draw both propagation steps and include the mechanism arrows for each step. H CH ot CH3 CI-CI MM hv of CH H-CI CH3 2nd attempt See Periodic Table See Hint Draw only radical electrons; do not add lone pair electrons. Note that arrows cannot meet in "space," and must end at either bonds or at atoms. 1 i Add the missing curved arrow notation to this propagation step. 20 H ن S F P H CI Br 品arrow_forwardThe radical below can be stabilized by resonance. 4th attempt Draw the resulting resonance structure. DOCEarrow_forward
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY