Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 10.8, Problem AQ
Interpretation Introduction
Interpretation:
Common role of the Chromium containing group, periodinane, and the dimethyl sulfide of the given reaction has to be discussed.
Concept Introduction:
Oxidation of alcohols: Oxidation of primary alcohol gives an
Leaving group: Leaving group can be any groups or atoms that get detached from either neutral or charged organic compounds. The stability of the leaving group is to stabilize the electron density that results from heterolysis cleavage of bond.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
10. The following reactions are all Lewis acid-base reactions. Remember that Lewis acids are electron pair acceptors. Lewis bases are electron pair donors. All the lone pairs are shown for the compounds below! For each reaction, label the acid and the base. Then use curved arrows to show the flow of electrons. Draw the product(s) of each reaction.
How is nucleophilicity (nucleophile strength) related to basicity?
A nucleophile donates a pair of electrons to form a new bond in a reaction. A
nucleophile is also considered a Lewis base and must have a lone pair to donate.
Identify which of the following compounds can act as a nucleophile.
Br
II.
OH
CH3
III. H3C Si-CH3
IV.
CH3
V.
A) I and II
B) I, II, and V
C) II and IV
D) II, III and IV
E) I and V
Give detailed Solution with explanation
needed of all options...don't give
Handwritten answer
Chapter 10 Solutions
Organic Chemistry
Ch. 10.1 - Write IUPAC names for these alcohols and include...Ch. 10.1 - Classify each alcohol as primary, secondary, or...Ch. 10.1 - Write IUPAC names for these unsaturated alcohols.Ch. 10.2 - Arrange these compounds in order of increasing...Ch. 10.2 - Prob. 10.5PCh. 10.4 - Predict the position of equilibrium for this...Ch. 10.5 - Show how to convert (R)-2-pentanol to...Ch. 10.6 - Draw structural formulas for the alkenes formed by...Ch. 10.6 - Propose a mechanism to account for this...Ch. 10.7 - Propose a mechanism to account for the following...
Ch. 10.7 - Prob. AQCh. 10.7 - Prob. BQCh. 10.7 - Prob. CQCh. 10.7 - Prob. DQCh. 10.7 - Which step in the reaction would you expect to be...Ch. 10.7 - Prob. FQCh. 10.7 - Prob. GQCh. 10.8 - Prob. 10.11PCh. 10.8 - Prob. AQCh. 10.8 - Prob. BQCh. 10.8 - Prob. CQCh. 10.8 - Why does nature use a reagent as complex as NAD+...Ch. 10.8 - -Hydroxyketones and -hydroxyaldehydes are also...Ch. 10.9 - Write IUPAC names for these thiols.Ch. 10 - Which are secondary alcohols?Ch. 10 - Name each compound.Ch. 10 - Prob. 10.16PCh. 10 - Name and draw structural formulas for the eight...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Prob. 10.20PCh. 10 - Prob. 10.21PCh. 10 - Arrange the compounds in each set in order of...Ch. 10 - Prob. 10.23PCh. 10 - The decalinols A and B can be equilibrated using...Ch. 10 - Prob. 10.25PCh. 10 - Select the stronger acid from each pair and...Ch. 10 - Prob. 10.27PCh. 10 - In each equilibrium, label the stronger acid, the...Ch. 10 - Write equations for the reaction of 1-butanol with...Ch. 10 - Write equations for the reaction of 2-butanol with...Ch. 10 - Prob. 10.31PCh. 10 - When (R)-2-butanol is left standing in aqueous...Ch. 10 - Two diastereomeric sets of enantiomers, A/B and...Ch. 10 - Acid-catalyzed dehydration of 3-methyl-2-butanol...Ch. 10 - Show how you might bring about the following...Ch. 10 - Propose a mechanism for the following pinacol...Ch. 10 - Prob. 10.37PCh. 10 - Show how each alcohol or diol can be prepared from...Ch. 10 - Dihydropyran is synthesized by treating...Ch. 10 - Show how to convert propene to each of these...Ch. 10 - Prob. 10.41PCh. 10 - Prob. 10.42PCh. 10 - The tosylate of a primary alcohol normally...Ch. 10 - Prob. 10.44PCh. 10 - Show how to convert cyclohexene to each compound...Ch. 10 - Prob. 10.46PCh. 10 - Ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3)...Ch. 10 - Prob. 10.48PCh. 10 - Prob. 10.49PCh. 10 - Prob. 10.50PCh. 10 - Write the products of the following sequences of...Ch. 10 - Alcohols are important for organic synthesis,...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59P
Knowledge Booster
Similar questions
- Explain the function of the acid in the second step.arrow_forwardIdentify the set of reaction conditions that best facilitates this reaction. Select the single best answer.arrow_forward4. Acid Chlorides. Fill in the missing reagents or products. Indicate the section where each reaction can be found. (From Chapter 20- Reaction Wheel) A B 1. xs LIAIH4 2. H₂O H SOCI₂, pyr. 1. LiAl(OtBu)3H 2. H₂O C XS NH2CH3 CI CH3OH pyr. G H₂O D 1. xs PhMgBr 2. H30* (CH3)2CuLi F Earrow_forward
- Alcohols are acidic in nature. Therefore, a strong base can abstract the acidic hydrogen atom of the alcohol in a process known as deprotonation. The alcohol forms an alkoxide ion by losing the proton attached to the oxygen atom of the hydroxyl ( -OH) group. The alkoxide formed can act as a base or a nucleophile depending on the substrate and reaction conditions. However, not all bases can abstract the acidic proton of alcohols and not all alcohols easily lose the proton. Deprotonation depends on the strength of the base and the acidity of the alcohol. Strong bases, such as NaNH2, can easily abstract a proton from almost all alcohols. Likewise, more acidic alcohols lose a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ► View Available Hint(s) CH3CH,OH + NH3 →CH,CH,O-NH CH3 CH3 H3C-C-H+NH3 → H3 C-C-H OH O-NH CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3 CHC12 Cl₂…arrow_forwardWhat does a value of K eq greater than 1 mean?A. More reactants than products exist at equilibrium.B. More products than reactants exist at equilibrium.C. The rate of the forward reaction is high atequilibrium.D. The rate of the reverse reaction is high atequilibrium.arrow_forwardFor the Reaction: NH3+ H2O = NH4+ OH- When adding NH3+ phenolphthalien+ HCl What stress is applied and what direction does the equilibrium shift? When adding NH3+ phenolphthalien+ NH4Cl What stress is applied and what direction does the equilibrium shift? When adding NH3+ phenolphthalien+ NaOH What stress is applied and what direction does the equilibrium shift? When adding NH3+ phenolphthalien+ HCl What stress is applied and what direction does the equilibrium shift?arrow_forward
- Chemistry complete for a rate. answer both questions for a rate 1. write out the mechanism for the reaction between ethyne and NaNH2. Label the acid snd the base predicting which way the reaction is favored. 2. do the same for C6H5OH and CH3CH2ONaarrow_forwardWhich of the following parameters affects the rate and kinetics of a reaction? A. Solvent medium B. Reaction temperature C. Reaction time D. Geometry and structure of the alkyl halide E. pHarrow_forwardIn each reaction box, place the best reagent and conditions from the list. 1) CEN 2) 3) 4) 5) Answer Bank NANH, NaBH, acetone CH,CH, MgBr (excess) acetic acid acetate ion CH,OH, H,O* (cat.) LIAIH, (CH,),CHMgBr (excess) CH,MgBr (excess) H,0 H,0*, H,0, heat acetyl chloridearrow_forward
- Do the following 8. In a reaction mechanism, a substance that is produced in one step, and consumed in a later step is a(n): Intermediate. Tranistion state. Catalyst. Starting material. 9. A substance that is present before and after the reaction takes place, and may increase the reaction rate by changing its mechanism is a(n): Catalyst. Intermediate. Starting material. Product. 12. An intermediate in an acid-catalyzed esterification has a partial _____ charge at its tetrahedral carbon center. positive negative 13. Water acts as a _______ in an acid-catalyzed esterification reaction. leaving group catalyst strong base None of these answers are correct 14. The number of particles with enough energy to overcome a chemical activation barrier ______ with increasing temperature. increases decreases remains the same 15. Because the pKa values of water and alcohols are very similar, the equilibrium constant for esterification reactions is close to _. 1 10 0.1 0arrow_forwardThe following enamine is in equilibrium with which compounds when in trace acidic conditions? a. 2-butene, N(CH3)2H b. 2-butanone, N(CH3)2H c. butanal, N(CH3)2H d. 2-butene-1-ol, LIAIH e. butanoic acid, N(CH3)2H N(CH3)2arrow_forward9:56 7 ← Question 9 of 25 Draw the major product of this reaction. Ignore inorganic byproducts. 1. PhMgBr 2. H3O+ Donearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENTOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning