10. Identify the reagents you would use to achieve of the following transformations Br Br OH CH 10. Predict the products obtained when 1-pentyne reacts with each of the following reagents (a) H2SO, H2O, HgSO, (b) 9-BBN followed by H2O2, Na OH (c) Two equivalents of HBr (e) Two equivalents of Br2 in CCla (A) NANH2 in NH3 followed by Mel (d) One equivalent of HCI (g) H2, Pt

10. Identify the reagents you would use to achieve of the following transformations Br Br OH CH 10. Predict the products obtained when 1-pentyne reacts with each of the following reagents (a) H2SO, H2O, HgSO, (b) 9-BBN followed by H2O2, Na OH (c) Two equivalents of HBr (e) Two equivalents of Br2 in CCla (A) NANH2 in NH3 followed by Mel (d) One equivalent of HCI (g) H2, Pt

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.65P: All rearrangements we have discussed so far have involved generation of an electron-deficient carbon...

See similar textbooks

Similar questions

All rearrangements we have discussed so far have involved generation of an electron-deficient carbon followed by a 1,2-shift of an atom or a group of atoms from an adjacent atom to the electron-deficient carbon. Rearrangements by a 1,2-shift can also occur following the generation of an electron-deficient oxygen. Propose a mechanism for the acid-catalyzed rearrangement of cumene hydroperoxide to phenol and acetone.
Write the appropriate reagents, conditions and products for the following transformations, in a single step. KMNO, OH', heat
8. Suggest a detailed step-by-step reaction mechanism for the reactions shown in a-b (use arrows to show electron flow). CH3 H3C CH3 (a) HO. ОН H,SO4 CH3 CH3 CH3OH CH3 (b) CH-I + HI OCH3
18. Identify the products from each step in the following synthesis sequence of reactions. Show the structure of all reactants and products from each step. (a) 3-methyl-1-pentanol + PBr3 --------> A (b) A + Mg/ether-------->B (c) B + 1.CH3CH2C(O)H/2.H3O+ -------> C (d) C + Na2Cr2O7/H2SO4, H2O -----> D
What is the correct sequence of steps for the following transformation? Step 1 Step 2 HO (a) HBr, followed by H20 (b) H2 over Lindlar's catalyst, followed by H2O/H,SO4 (c) H2O/H2SO4/H&SO4, followed by HBr (d) H2 over Pd/C, followed by H20 Which structure corresponds to the missing step in the reaction mechanism for the conversion of the alkene/alcohol to the cyclic ether? HC! H20 + H;O OH OH OH (a) (b) (c) (d)
4) Provide the reagents and/or reaction conditions necessary to effect each of the following transformations (reminder: more than one step might be necessary): NO2 Br HO. OH Br HO, OCH3 OH
The following series of reactions will yield 2) CI-CH2-CH2-C6H5 1) CH3CH2SH + N2OH O 2-chloro-4-ethyl-benzenesulfonic acid O CH;CH2-S-CH2CH2C6H5 O ortho-chloro-ethyl-benzene O 1-phenyl-3-chloro-propane O CH3CH2-O-CH2CH2C6H5
The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. ОН ОН p-TSCI CH,COO Na+ A 1. LIAIH, pyridine DMSO 2. H,О (R)-2-Octanol (S)-2-Octanol Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.
11. What is the product for the reaction shown? 요 (A) (B) (C) LIAIH4 H₂O, H+ CH3CCH₂CH=CH₂ ether 0 11 CH3CCH₂CH₂CH3 OH CH3CHCH₂CH=CH₂ он CH,CHCH,CH,CH3 (D) CH3CH₂OH + CH3CH₂CH3
Which of the following reactions will synthesize phenol from benzene? 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat 1) Acetyl chloride & AlCl3; 2) bleach 1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4 1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4
9. (a) Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second. What would be the rate if 0.1 M 1-bromobutane and 2.0 M NaOCH3 were used? (b) Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw the reactants, the transition state, and the products. Note that the initial product is the salt of an amine (RNH* Br) which is deprotonated by the excess ammonia to give the amine. (c) Show another SN2 reaction using a different combination of an alkoxide and an alkyl bromide that also produces 1-methoxybutane.
The reaction of 1-bromopropane and sodium hydroxide in ethanol occurs by an SN2mechanism. What happens to the rate of this reaction under the following conditions?(a) The concentration of NaOH is doubled.(b) The concentrations of both NaOH and 1-bromopropane are doubled.(c) The volume of the solution in which the reaction is carried out is doubled.