The carbon adjacent to a nitrile group (CN) can be deprotonated using LDA and alkylated with an alkyl halide, analogous tothe alkylation of ketones. Use this knowledge and apply it to design a synthetic plan that would suite the transformationshown below.МеBrOEtMeМеO 1) Mg 2) NaCN 3) MeBr 4) H30+, heat 5) E1OH, H2SO4 (catalytic)O 1) NaCN 2) MeMgBr 3) H3O+ 4) EtOH, H2SO4 (catalytic)O 1) NaCN 2) LDA 3) MeBr 4) LİAIH4 5) H3O*, heat 6) E1OH, H2S04 (catalytic)O 1) NACN 2) LDA 3) MeBr 4) H3O*, heat 5) E1OH, H2SO4 (catalytic)none of the other answer choices are correct

Applying concept of organic synthesis.

The carbon adjacent to a nitrile group (CN) can be deprotonated using LDA and alkylated with an alkyl halide, analogous to the alkylation of ketones. Use this knowledge and apply it to design a synthetic plan that would suite the transformation shown below. Me Br Me Me 1) Mg 2) NaCN 3) MeBr 4) H3O*, heat 5) EtOH, H2SO4 (catalytic) 1) NaCN 2) MeMgBr 3) H3O+ 4) EtOH, H2SO4 (catalytic) 1) NaCN 2) LDA 3) MeBr 4) LİAIH4 5) H3O*, heat 6) EtOH, H2SO4 (catalytic) 1) NaCN 2) LDA 3) MeBr 4) H3O†, heat 5) EtOH, H2SO4 (catalytic) none of the other answer choices are correct

The carbon adjacent to a nitrile group (CN) can be deprotonated using LDA and alkylated with an alkyl halide, analogous to the alkylation of ketones. Use this knowledge and apply it to design a synthetic plan that would suite the transformation shown below. Me Br Me Me 1) Mg 2) NaCN 3) MeBr 4) H3O, heat 5) EtOH, H2SO4 (catalytic) 1) NaCN 2) MeMgBr 3) H3O+ 4) EtOH, H2SO4 (catalytic) 1) NaCN 2) LDA 3) MeBr 4) LİAIH4 5) H3O, heat 6) EtOH, H2SO4 (catalytic) 1) NaCN 2) LDA 3) MeBr 4) H3O†, heat 5) EtOH, H2SO4 (catalytic) none of the other answer choices are correct

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter21: Nas: Nucleophilic Aromatic Substitution

Section: Chapter Questions

Problem 7E

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Similar questions

Organic chemistry student Everett has set up two separate electrophilic addition reactions with 2-butyne (shown below). In reaction (i) the alkyne is treated with 1 equivalent of HBr, which successful provides (Z)-2-bromo-2-butene. In reaction (ii) the alkyne is subjected to a two-step hydroboroation/oxidation sequence. Interestingly, Everett’s second reaction fails to provide the desired methyl ketone and instead has provided butan-2,3-diol. (a) Provide the structure of intermediate X form the first step of reaction (ii). (b) Briefly explain (use structures if necessary) why reaction (i) provided an alkene where as reaction (ii) provided an alkane when only 1 equivalent of the electrophile was used in each reaction.
Draw the products and necessary reagents of the three step retrosynthetic reaction sequence shown below. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. Please choose from the following options for each of the reagents. (top reagents options) A. HNO3, cat. H2SO4 B. SO3, cat. H2SO4 C. CH3C(=O)Cl, AlCl3 D. Cl2, FeCl3 E. H2O, HCl (reagents option to the right) (top reagents options) A. HNO3, cat. H2SO4 B. SO3, cat. H2SO4 C. CH3C(=O)Cl, AlCl3 D. Cl2, FeCl3 E. H2O, HCl
Which of the following statements is TRUE regarding the reaction below? Options: The IR spectrum of the major organic product will show a broad absorption between 3000-3500 cm-1. The mass spectrum of the major organic product will show an M+2 peak in the molecular ion region. The reaction should proceed without carbocation rearrangement. The alkene is the electrophile and water is the nucleophile in the first step. HSO4- is the dominant nucleophile in the second step.
In the early age of the development of Organometallilc Chemistry, the preparation of Organometallic Compound containing M-R(R: alkyl group) bond always led to the decomposition of the M-R bond. It was later known to be caused by the so called “beta-hydrogen elimination” process. Which of the following statements is not correct? This process can be prevented by using all halogenated alkyl group. This process can be prevented by carrying out reaction at high temperature. The Grignard’s reagent, RMgX or R2Mg is stable and does not undergo “b-hydrogen elimination” process. The anti-knocking agent, Pb(C2H5)4 is stable and does not undergo “b-hydrogen elimination” process. The ferrocene, Cp2Fe, is free from the “b-hydrogen elimination” process.
Provide a retrosynthesis (with complete reaction conditions) of the followingcompound from alkyl halides containing 6 carbons or less. The starting materials may be any type of alkyl halide (primary, secondary, or tertiary). You may use any other reagents you find necessary.
Synthesise the target molecules drawn below using precursor chemicals within the following limitations: 1) ALL intermediates and reagents must be shown.2) Each molecule requires multiple step synthesis.3) You must also synthesize any organometallic reagents or ligands that you wish to use. b) Use any precursor molecules with 7 carbon atoms or less.
The two Grignard reactions and the reduction reaction below are all believed to have similar mechanisms. Use the curved arrow formalism to draw a single mechanism for these reactions using :Nuc-1 to indicate the nucleophile. The reacations are: cyclohexylmagnesium chloride + acetone in ether --> 2-cyclohexyl-2-propanol phenylmagnesium bromide + acetone in ether --> 2-phenyl-2-propanol Acetone + NaBH4 --> 2-propanol
(True/False) The use of sodium iodide in acetone promotes SN2 mechanism for alkyl halide resulting in the formation of insoluble salts in the mixture. (True/false) For alkyl halides, we use a solution of AgNO3 in ethanol because ethanol is a polar protic solvent suited for SN1 mechanism. (True/False) 1-bromobutane, 2-bromobutane (aka sec-butyl bromide), tert-butyl bromide, benzyl chloride, and bromobenzene will not form precipitates in either 1M NaI/acetone and 2% AgNO3/EtOH.
Draw Out Your Predictions of This Reaction: Part A: S-2-chlorohexane + NaOCH3NaOCH3 in methanol. (There are three elimination products and one substitution product.) Part B: 2-chloro-2-methylbutane heated in ethanol
Choose the best reagents from the list provided below for carrying out the following conversion. Match the reagent with the step number. HCl (aq), Zn(Hg) KMnO4, H3O+ CH3Cl, AlCl3 HNO3, H2SO4 Cl2, FeCl3 fuming sulfuric acid
Several reagents and several organic structures are shown below. Construct a multistep synthetic route from the reactant 2-methyl-1-butene to the product 3-bromo-2-methyl-2-butanol by dragging the appropriate pieces into the bins. Note that each bin will hold only one item, and not every given reagent or structure will be used.
What is the major neutral organic product for the following transformation?