ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 7.18, Problem 7.35P
(a)
Interpretation Introduction
To determine: The product and the mechanism of the dehydration of the given alcohol if it is heated in the presence of sulfuric or phosphoric acid.
Interpretation: The product and the mechanism of the dehydration of the given alcohol if it is heated in the presence of sulfuric or phosphoric acid is to be stated.
Concept introduction: The
In acid-catalyzed dehydration, a saturated compound is converted to an unsaturated compound in the presence of an acid catalyst.
(b)
Interpretation Introduction
To determine: The product and the mechanism of the dehydration of the given alcohol if it is heated in the presence of sulfuric or phosphoric acid.
Interpretation: The product and the mechanism of the dehydration of the given alcohol if it is heated in the presence of sulfuric or phosphoric acid is to be stated.
Concept introduction: The chemical reaction that consists of an alkyl halide, a good leaving group, reacts with Lewis base to form an alkene is termed as elimination reaction. In this reaction there is complete removal of the leaving group without any substitution.
In acid-catalyzed dehydration, a saturated compound is converted to an unsaturated compound in the presence of an acid catalyst.
(c)
Interpretation Introduction
To determine: The product and the mechanism of the dehydration of the given alcohol if it is heated in the presence of sulfuric or phosphoric acid.
Interpretation: The product and the mechanism of the dehydration of the given alcohol if it is heated in the presence of sulfuric or phosphoric acid is to be stated.
Concept introduction: The chemical reaction that consists of an alkyl halide, a good leaving group, reacts with Lewis base to form an alkene is termed as elimination reaction. In this reaction there is complete removal of the leaving group without any substitution.
In acid-catalyzed dehydration, a saturated compound is converted to an unsaturated compound in the presence of an acid catalyst.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following
compounds. Please show your work. (8) SF2, CH,OH, C₂H₂
b) Based on your answers given above, list the compounds in order of their Boiling Point
from low to high. (8)
19.78 Write the products of the following sequences of reactions. Refer to your reaction road-
maps to see how the combined reactions allow you to "navigate" between the different
functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18
roadmaps along with your new Chapter 19 roadmap for these.
(a)
1. BHS
2. H₂O₂
3. H₂CrO4
4. SOCI₂
(b)
1. Cl₂/hv
2. KOLBU
3. H₂O, catalytic H₂SO4
4. H₂CrO4
Reaction
Roadmap
An alkene 5. EtOH
6.0.5 Equiv. NaOEt/EtOH
7. Mild H₂O
An alkane
1.0
2. (CH3)₂S
3. H₂CrO
(d)
(c)
4. Excess EtOH, catalytic H₂SO
OH
4. Mild H₂O*
5.0.5 Equiv. NaOEt/EtOH
An alkene 6. Mild H₂O*
A carboxylic
acid
7. Mild H₂O*
1. SOC₁₂
2. EtOH
3.0.5 Equiv. NaOEt/E:OH
5.1.0 Equiv. NaOEt
6.
NH₂
(e)
1. 0.5 Equiv. NaOEt/EtOH
2. Mild H₂O*
Br
(f)
i
H
An aldehyde
1. Catalytic NaOE/EtOH
2. H₂O*, heat
3. (CH,CH₂)₂Culi
4. Mild H₂O*
5.1.0 Equiv. LDA
Br
An ester
4. NaOH, H₂O
5. Mild H₂O*
6. Heat
7.
MgBr
8. Mild H₂O*
7. Mild H₂O+
Li+ is a hard acid. With this in mind, which if the following compounds should be most soluble in water?
Group of answer choices
LiBr
LiI
LiF
LiCl
Chapter 7 Solutions
ORGANIC CHEMISTRY
Ch. 7.3A - Prob. 7.1PCh. 7.3A - Prob. 7.2PCh. 7.3B - Draw five more compounds of formula C4H6NOC1.Ch. 7.3B - For each of the following molecular formulas,...Ch. 7.4 - Give the systematic (IUPAC) names of the following...Ch. 7.5B - The following names are all incorrect. Draw the...Ch. 7.5B - Prob. 7.8PCh. 7.5B - a. How many stereogcmc double bonds are in...Ch. 7.6 - Teflon-coated frying pans routinely endure...Ch. 7.7B - Prob. 7.11P
Ch. 7.8B - Use the data in Table7-2 to predict the energy...Ch. 7.8C - Prob. 7.13PCh. 7.8E - Explain why each of the following alkenes is...Ch. 7.8F - Prob. 7.15PCh. 7.10 - Prob. 7.16PCh. 7.10A - SN1 substitution and E1 elimination frequently...Ch. 7.10C - Prob. 7.18PCh. 7.10C - Prob. 7.19PCh. 7.10C - Prob. 7.20PCh. 7.11 - Prob. 7.21PCh. 7.11 - Prob. 7.22PCh. 7.12 - Prob. 7.23PCh. 7.12 - Prob. 7.24PCh. 7.13 - Prob. 7.25PCh. 7.14B - Prob. 7.26PCh. 7.14B - Make models of the blowing compounds, and predict...Ch. 7.15 - Prob. 7.28PCh. 7.15 - Prob. 7.29PCh. 7.15 - Prob. 7.30PCh. 7.15 - Prob. 7.31PCh. 7.16 - Predict the major and minor elimination products...Ch. 7.17B - Predict the products and mechanisms of the...Ch. 7.18 - Propose mechanisms for the following reactions.Ch. 7.18 - Prob. 7.35PCh. 7.19B - The dehydrogenation of butane to trans-but-2-ene...Ch. 7.19B - Prob. 7.37PCh. 7.19B - Prob. 7.38PCh. 7.19B - Prob. 7.39PCh. 7 - Prob. 7.40SPCh. 7 - Prob. 7.41SPCh. 7 - Prob. 7.42SPCh. 7 - Prob. 7.43SPCh. 7 - Prob. 7.44SPCh. 7 - Prob. 7.45SPCh. 7 - Prob. 7.46SPCh. 7 - The energy difference between cis- and...Ch. 7 - Prob. 7.48SPCh. 7 - Prob. 7.49SPCh. 7 - Prob. 7.50SPCh. 7 - What halides would undergo E2 dehydrohalogenation...Ch. 7 - Prob. 7.52SPCh. 7 - Prob. 7.53SPCh. 7 - Write a balanced equation for each reaction,...Ch. 7 - Prob. 7.55SPCh. 7 - Using cyclohexane as your starting material, show...Ch. 7 - Show how you would prepare cyclopentene from each...Ch. 7 - Prob. 7.58SPCh. 7 - E1 eliminations of alkyl halides are rarely useful...Ch. 7 - Prob. 7.60SPCh. 7 - Propose mechanisms for the following reactions....Ch. 7 - Prob. 7.62SPCh. 7 - Prob. 7.63SPCh. 7 - Prob. 7.64SPCh. 7 - Prob. 7.65SPCh. 7 - Prob. 7.66SPCh. 7 - Prob. 7.67SPCh. 7 - Prob. 7.68SPCh. 7 - Prob. 7.69SPCh. 7 - Explain the dramatic difference in rotational...Ch. 7 - One of the following dichloronorbornanes undergoes...Ch. 7 - A graduate student wanted to make...Ch. 7 - Prob. 7.73SPCh. 7 - Prob. 7.74SPCh. 7 - Prob. 7.75SPCh. 7 - Prob. 7.76SP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Q4: Write organic product(s) of the following reactions and show the curved-arrow mechanism of the reactions. Br MeOH OSO2CH3 MeOHarrow_forwardProvide the correct IUPAC name for the compound shown here. Reset cis- 5- trans- ☑ 4-6- 2- 1- 3- di iso tert- tri cyclo sec- oct but hept prop hex pent yl yne ene anearrow_forwardQ6: Predict the major product(s) for the following reactions. Note the mechanism (SN1, SN2, E1 or E2) the reaction proceeds through. If no reaction takes place, indicate why. Pay attention to stereochemistry. NaCN DMF Br σ Ilm... Br H Br H H NaCN CH3OH KOtBu tBuOH NaBr H₂O LDA Et2O (CH3)2CHOH KCN DMSO NaOH H₂O, A LDA LDA Systemarrow_forward
- Q7: For the following reactions, indicate the reaction conditions that would provide the indicated product in a high yield. Note the major reaction pathway that would take place (SN1, SN2, E1, or E2) Note: There may be other products that are not shown. There maybe more than one plausible pathway. Br H3C OH H3C CI ... H3C SCH2CH3 CI i SCH2CH3 ཨ་ Br System Settarrow_forwardQ2: Rank the compounds in each of the following groups in order of decreasing rate of solvolysis in aqueous acetone. OSO2CF3 OSO2CH3 OH a. b. CI Brarrow_forwardох 4-tert-butyl oxy cyclohex-1-ene Incorrect, 1 attempt remaining The systematic name of this compound classifies the -OR group as a substituent of the hydrocarbon, which is considered the principal functional group. The ether substituent is named with the suffix 'oxy'. The general format for the systematic name of a hydrocarbon is: [prefix/substituent] + [parent] + [functional group suffix] Substituents are listed in alphabetical order. Molecules with a chiral center will indicate the absolute configuration at the beginning of its name with the R and S notation.arrow_forward
- 5. Compressibility (6 points total). The isothermal compressibility is a measure of how hard/easy it is to compress an object (how squishy is it?) at constant temperature. It is др defined as Br=-()=-(200²)T' (a) You might wonder why there is a negative sign in this formula. What does it mean when this quantity is positive and what does it mean when this quantity is negative? (b) Derive the formula for the isothermal compressibility of an ideal gas (it is very simple!) (c) Explain under what conditions for the ideal gas the compressibility is higher or lower, and why that makes sense.arrow_forward19. (3 pts) in Chapter 7 we will see a reaction of halocyclohexanes that requires that the halogen occupy an axial position with this in mind, would you expect cis-1-bromo-3-methylcyclohexane or trans-1-bromo-3-methylcyclohexane to be more reactive in this reaction? Briefly explain your choice using structures to support your answer. Mere-eries-cecleone) The tran-i-browse-3-methylcyclohexionearrow_forwardPlease help me calculate the undiluted samples ppm concentration. My calculations were 280.11 ppm. Please see if I did my math correctly using the following standard curve. Link: https://mnscu-my.sharepoint.com/:x:/g/personal/vi2163ss_go_minnstate_edu/EVSJL_W0qrxMkUjK2J3xMUEBHDu0UM1vPKQ-bc9HTcYXDQ?e=hVuPC4arrow_forward
- Provide an IUPAC name for each of the compounds shown. (Specify (E)/(Z) stereochemistry, if relevant, for straight chain alkenes only. Pay attention to commas, dashes, etc.) H₁₂C C(CH3)3 C=C H3C CH3 CH3CH2CH CI CH3 Submit Answer Retry Entire Group 2 more group attempts remaining Previous Nextarrow_forwardArrange the following compounds / ions in increasing nucleophilicity (least to most nucleophilic) CH3NH2 CH3C=C: CH3COO 1 2 3 5 Multiple Choice 1 point 1, 2, 3 2, 1, 3 3, 1, 2 2, 3, 1 The other answers are not correct 0000arrow_forwardcurved arrows are used to illustrate the flow of electrons. using the provided starting and product structures, draw the cured electron-pushing arrows for thw following reaction or mechanistic steps. be sure to account for all bond-breaking and bond making stepsarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Lipids - Fatty Acids, Triglycerides, Phospholipids, Terpenes, Waxes, Eicosanoids; Author: The Organic Chemistry Tutor;https://www.youtube.com/watch?v=7dmoH5dAvpY;License: Standard YouTube License, CC-BY