Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 12, Problem 36P
Interpretation Introduction

Interpretation:

The starting material that led to the given product through the defined reactions is to be deduced.

Concept introduction:

Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron rich species that have negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has unpaired electrons, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

The Grignard reagent or RMgX is a polar organometallic reagent that undergoes nucleophilic addition reaction with aldehydes and ketones. It contains organic group which is covalently bonded to magnesium atom, which is also bonded to halogen atom.

Grignard reagent or RMgX can be synthesized from haloalkanes by reacting them with magnesium in the presence of dry ether.

Grignard reagent or RMgX is a reagent that can be prepared from alkyl halide and magnesium in the ether. It adds on the alkyl group to carbonyl moiety and converts aldehydes or ketones to alcohols. The reaction of cyanides with RMgX forms ketones. It reacts with carbon dioxide to form a carboxylic acid.

Alkynes undergo conversion to cis-alkenes by Lindlar’s catalyst.

Elimination reaction of halo alkanes with potassium tertbutoxide can form alkenes.

Hydroxyl group of alcohol can undergo substitution to form halogen derivatives with reagents like MsCl or PBr3.

Halogenation can occur at allylic or benzylic positions of existing double bonds by using reagents like NBS.

Swern oxidation is a reaction that involves the conversion of alcohol to the aldehyde by treating alcohol with DMSO and oxalyl chloride at very low temperature.

The OH group is replaced by Br on reaction with PBr3.

Alkene is converted into alcohol on reaction with THF and water.

Alkene is converted into alkane in presence of H2/Pt, Pd or Ni.

Alcohol can be converted into aldehyde in the presence of DMSO, Et3N, or PCC. CH2Cl2

Secondary alcohol can be converted into ketone on reaction with H2CrO4, acetone and water.

Primary alcohol can be converted into carboxylic acid on reaction with (i) KMnO4,HO and heat, (ii) H3O+

Primary alcohol can be converted into ether on reaction with sulfuric acid at 140°C .

Grignard reagent reacts with a ketone in the presence of NH4Cl/H2O to form an alcohol.

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(a) (b) (c) Suggest a synthesis of the following alkene (A) using a Wittig reaction strategy. Draw the starting material(s), key reagent and a full reaction mechanism including an explanation of the observed geometry. Which of the following (B) and (C) will favour the enol form? Briefly explain your reasoning. Predict the product(s) and provide a mechanism for each of the following transformations: (i) (ii) OMe OMe Base OEt NaOEt
Write equations showing how to prepare each of the following from benzene or toluene and any necessary organic or inorganic reagents. If an ortho, para mixture is formed in any step of your synthesis, assume that you can separate the two isomers. (a) Isopropylbenzene (b) p-Isopropylbenzenesulfonic acid (c) 2-Bromo-2-phenylpropane (d) 4-tert-Butyl-2-nitrotoluene (e) m-Chloroacetophenone (f) p-Chloroacetophenone (g) 3-Bromo-4-methylacetophenone (h) 2-Bromo-4-ethyltoluene (i) 3-Bromo-5-nitrobenzoic acid (j) 2-Bromo-4-nitrobenzoic acid (k) 1-Phenyloctane (l) 1-Phenyl-1-octene (m) 1-Phenyl-1-octyne (n) 1,4-Di-tert-butyl-1,4-cyclohexadiene
Provide concise syntheses for each of the following compounds starting from but-1 - ene. The source of all the carbon atoms in these molecules must be either but-1 - ene or any one carbon nucleophile/electrophile. (If you must use a reagent that has more than one carbon atoms you must show the preparation of that reagent from but-1 - ene.) (a) Methyl propanoate (b) 3, 5- Dimethylheptan-4-one (c) 5-ethyl-7-methylnon-4-ene

Chapter 12 Solutions

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