Concept explainers
(a)
Interpretation:
For the given nitration reaction, orientation of the reaction has to be accounted.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of
Activating groups – ortho/para directing groups. The
Deactivating groups – meta directing groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
(b)
Interpretation:
For the given substitution reaction in step 2, reaction mechanism has to be proposed.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.
Activating groups – ortho/para directing groups. The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.
Deactivating groups – meta directing groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
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Chapter 22 Solutions
Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- (b) Propose a synthesis of (2,2-dimethylpropyl)benzene from benzene.arrow_forwardExplain the mechanism of the following reactions :(i) Addition of Grignard’s reagent to the carbonyl group of a compound forming an adduct followed by hydrolysis.(ii) Acid catalysed dehydration of an alcohol forming an alkene.(iii) Acid catalysed hydration of an alkene forming an alcohol.arrow_forward(a) Give an acceptable name for compound A. (b) Draw the organic products formed when A is treated with each reagent: [1] H3O+; [2] −OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.arrow_forward
- (a) Draw the mechanism for the formation of both of the enols that can be formed from A (use acetic acid & AcOH as the source of the protons) (b) Draw the mechanism of reaction of this enol with bromine to give product Barrow_forwardRank the compounds in each group in order of increasing reactivity in electrophilic aromatic substitution: (a) C6H6, C6H5Cl, C6H5CHO; (b) C6H5CH3, C6H5NH2, C6H5CH2NH2.arrow_forward(a) 4 Choose the major product of the following elimination. (b) OH H₂SO4 heat (c) (d) 1 ptsarrow_forward
- (a) Propose a reasonable synthesis for the formation of nonane from CH3CH2CH2I and any other organic/inorganic reagent. (b) Suggest three (3) different Grignard reactions leading to 2-phenyl-2-butanol.arrow_forward(b) (c) Suggest a synthesis of the following compound (D) which utilises a conjugate addition strategy. Explain your reasoning clearly by drawing the mechanism. D Ph3P Me Predict the product and provide a mechanism for each of the following transformations; (i) Harrow_forward(b) State the reagents needed to convert benzoic acid into the following compounds. (i) C6H§COCI (ii) C,H$CH2OH (iii) C6H$CONHCH3arrow_forward
- (d) (i) Identify products B-F in the following reaction scheme. (ii) Provide a mechanism for the formation of B from benzene. (iii) Provide a mechanism for the formation of C from B. H2SO4 Brz B C FeBr3 Brz FeBrз H2SO4 D E & Farrow_forwardFor each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (SN1) or second order (SN2). (a) cyclohexyl bromide + methanolarrow_forward(a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning