Compounds containing deuterium (D = 2H) are useful for kinetic studies and metabolic studies with new pharmaceuticals.One way to introduce deuterium is by using the reagent LiAlD4, equivalent in reactivity to LiAlH4. Show how to makethese deuterium-labeled compounds, using LiAlD4 and D2O as your sources of deuterium, and any non-deuterated startingmaterials you wish.(a) CH3CHDOH (b) CH3CD2OH (c) CH3CD2OD

Compounds containing deuterium (D = 2H) are useful for kinetic studies and metabolic studies with new pharmaceuticals.One way to introduce deuterium is by using the reagent LiAlD4, equivalent in reactivity to LiAlH4. Show how to makethese deuterium-labeled compounds, using LiAlD4 and D2O as your sources of deuterium, and any non-deuterated startingmaterials you wish.(a) CH3CHDOH (b) CH3CD2OH (c) CH3CD2OD

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

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.47P: When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and...

See similar textbooks

Similar questions

3. Outline a synthetic scheme for the preparation of the compounds A from the suggested starting material by the suggested method. Make sure to clearly indicate all reagents needed to perform each step of the synthetic scheme. (a) OH O=S=O Br A (b) H₂N. (c) HO3S. Br Br A A 1 Br
Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures. (a) 3-nitro-4-bromobenzoic acid (b) 3-nitro-5-bromobenzoic acid (c) 4-butylphenol (d) 2-(4-methylphenyl)butan-2-ol
2B Suggest a short synthetic route for the preparation of compound D from compound C OH Br COOH C D Note: Apart from compound C, you can also use organic reagents with up to 1 C atom. The number of arrows in the figure above does not necessarily correspond to the number of steps.
Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.
1. (a) Oxidation of 1-butanol with PCC will produce which of the following? 2-chlorobutanal butanone butanoic acid butanal (b) Which synthetic route is the best way to prepare ethyl isopropyl ether? CH3CH2OH + (CH3)2CHOH + H2SO4, 140 oC CH3CH2ONa + (CH3)2CHOH CH3CH2ONa + (CH3)2CHBr (CH3)2CHONa + CH3CH2Br (c) The Williamson ether synthesis involves nucleophilic substitution involving an alkyl halide and an alcohol. (True or False)
1. (a) Oxidation of 1-butanol with PCC will produce which of the following? 2-chlorobutanal butanone butanoic acid butanal (b) Which synthetic route is the best way to prepare ethyl isopropyl ether? CH3CH2OH + (CH3)2CHOH + H2SO4, 140 oC CH3CH2ONa + (CH3)2CHOH CH3CH2ONa + (CH3)2CHBr (CH3)2CHONa + CH3CH2Br
Suggest readily available starting materials and reaction conditions suitable for obtaining each of the following compounds by a procedure involving alkylation of nucleophilic carbon. (a) PHCH2CH2CHPH (b) (CH3)½C=CHCH2CH2CCH2CO;CH3 ČN (c) (d) CH2=CHCH=CHCH2CH2CO,H CH3 CH2CO2H CH3 CH3CO CH;CH2CH2 (f) (e) 2,3-diphenylpropanoic acid (g) CH3Oʻ CH3CH2 CH2CH=CH2
Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. (1) (2) (3) OH (4) 2-ethoxy-1-butanol (racemic) OH OH (c) ethylene oxide Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: (a) (CH3)3 COK+, THF (d) H₂SO4, H₂O (b) OsO4, H₂O2 Br OH (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate (PCC) + 2 Oly (i) PBr3 (9) H₂SO4 (anhydrous) (h) NaOH (j) Na, NH3 (1) (k) NBS, heat (N-bromosuccinimide) Previous Next Save and Exit ?
9. Plan syntheses of the following compounds. You may use the given starting material and any compound containing three or fewer carbons. (a) (b) (c) (d) by Br or Br H Br H OH = OH
P4B. Using the shown starting material and acetylene, suggest the most appropriate synthetic method for the following reaction:
Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. (1) (2) (3) OH (4) 2-ethoxy-1-butanol (racemic) OH OH (c) ethylene oxide Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: (a) (CH3)3 CO K+, THF (d) H₂SO4, H₂O (b) OsO4, H₂O2 1 Br (e) m-chloroperoxybenzoic acid OH (mCPBA) (f) pyridinium chlorochromate (PCC) + le 2 (9) H₂SO4 (anhydrous) (j) Na, NH3 (1) (h) NaOH (k) NBS, heat (i) PBr3 (N-bromosuccinimide) Previous Next
The following bicyclic ketone has two -carbons and three -hydrogens. When this molecule is treated with D2O in the presence of an acid catalyst, only two of the three -hydrogens exchange with deuterium. The -hydrogen at the bridgehead does not exchange. How do you account for the fact that two -hydrogens do exchange but the third does not? You will find it helpful to build models of the enols by which exchange of -hydrogens occurs.