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

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 50AP: -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the...

See similar textbooks

Similar questions

Benzene, C6H6 undergoes substitution reaction with concentrated nitricacid, HNO3 to produce compound L. The reaction of compound L withbromine, Br2 in the presence of iron tribromide, FeBr3 produced compoundM. Benzene also undergoes Fridel-crafts alkylation reaction withchloroethane, CH3CH2Cl using catalyst N to produce compound P (i) Draw the structural formula of L, M and P (ii) State catalyst N. (iii) Show the formation of electrophile that will be reacted with benzene for theformation of compound P.
The sex attractant of the housefly has the formula C23 H46. When treated with warm potassium permanganate, this phero- mone gives two products: CH3(CH2)12COOH and CH3(CH2)7COOH. Suggest a structure for this sex attractant. Explain which part of the structure is uncertain.
1.Describe the ozonolysis of alkenes 2.one mole of a hydrocarbon(A) reacts with one mole of beomine giving a dibromo compound C5H10Br2.Substance A on treatment with cold dilute kMnO4 solution forms a compound C5C12O2(C5H12O2) on ozonolysis A,gives equimolar quantities of propanone and ethanol.Deduce the structure of substance A.
1. Compound A, C9H12, absorbs 3 equivalents of H2 on catalytic hydrogenation over palladium catalyst to give B, C9H18. On the treatment with acidic KMnO4, compound A gives among other things, a ketone that was identified as cyclohexanone. On reaction with NaNH2 in NH3, followed by addition of iodomethane, compound A gives a new hydrocarbon C, C10H14. What are the structures of A , B and C?
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.
-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.
(19, 8, 3) Specify a synthetic scheme that would produce the compound shown above in the fewest steps possible. Use one of the starting materials shown together with any of the available reagents. Give the number of the starting material followed by the letters of the reagents in the order of their use, for example: 3be.
A key step in the synthesis of naproxen, an NSAID more commonly known by its brand name, Aleve (Section 3.9), is a coupling reaction of 2-bromo-6-methoxynaphthalene to form 2-methoxy-6-vinylnaphthalene. Show three different coupling reactions, and the required reagents, that could be used tocarry out this step.
we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?
Stearolic acid, C18H32O2, yields stearic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield nonanoic acid and nonanedioic acid. What is the structure of stearolic acid?
Give the reagents and conditions to provide the following transformations, usethe 1. 2. etc. notations as appropriate
7. Compound AA, C4H8O, gives a positive result (formation of a silver mirror) when reacted with Tollen’s reagent. Reduction of compound AA with lithium aluminium hydride, LiAlH4 followed by acidified water, H3O+ produces an alcohol, BB. Oxidation of BB with hot acidified potassium dichromate, K2Cr2O7 gives butanoic acid, C3H7COOH. Esterification between butanoic acid and methanol, CH3OH produces compound CC. Dehydration of compound BB using concentrated sulphuric acid, H2SO4 at a temperature of 180°C produces compound DD. Draw the structural formula of compounds AA, BB, CC, and DD