Concept explainers
(a)
Interpretation:
The stereochemistry of product formed from more stable intermediate is to be predicted.
Concept introduction:
The replacement or substitution of one
(b)
Interpretation:
The stereochemistry of product formed from less stable intermediate is to be predicted.
Concept introduction:
The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. In nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking on the electron deficient carbon atom.
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Organic Chemistry
- (i) Explain why a high reaction temperature favours elimination reactions, instead of substitution reactions. (ii) Explain why polar aprotic solvents favour Sn2 reaction but not favour SN1 reaction.arrow_forward2) The Diels-Alder reaction, developed by German chemists Otto Diels and Kurt Alder (who received the Nobel Prize in 1950 for their discovery), has great synthetic importance due to the possibility of forming an unsaturated six-membered cycle without involving intermediates ionic. About the reaction, answer: (a) Indicate the reagents necessary for the synthesis of the following compounds, indicating who is the diene and who is the dienophile.arrow_forward(i) State one use each of DDT and iodoform.(ii) Which compound in the following couples will react faster in SN2 displacement and why?(a) 1-bromopentane or 2-bromopentane(b) l-bromo-2-methylbutane or 2-bromo-2-methylbutane.arrow_forward
- Which alkyl halide in each of the following pairs will react faster in an SN2 reaction with OH? Explain your answer briefly. (a) Bromobenzene or benzyl bromide, C6H5CH2B. (b) CH3C1 or (CH3)3CCI (c) CH3CH=CHBr or H2C=CHCH2BRarrow_forward(a) Give a mechanism for this reaction, showing how the two products arise as aconsequence of the resonance-stabilized intermediate.(b) The bromination of cyclohexene using NBS gives only one major product, as shown onthe previous page. Explain why there is no second product from an allylic shift.arrow_forward8.23 In each of the following indicate which reaction will occur faster. Explain your reasoning. (D) Solvolysis of 1-bromo-2,2-dimethylpropane or tert-butyl bromide in ethanol (E) Solvolysis of isobutyl bromide or sec-butyl bromide in aqueous formic acid (F) Reaction of 1-chlorobutane with sodium acetate in acetic acid or with sodium methoxide in methanolarrow_forward
- (a) Identify the major product of the following reaction. (b) Explain why the other product is not the major product.arrow_forward(a) Which of the following phenols is the least acidic? (b) Which of the following phenols is the most acidic?arrow_forwardWhich alkene would give a single compound (not a mixture of enantiomers and/or diastereomers) as the major organic product upon reaction with HBr in the presence of peroxide and light?arrow_forward
- When butane reacts with Br₂ in the presence of Cl₂, both brominated and chlorinated products are obtained. Under such conditions, the usual selectivity of bromination is not observed. In other words, the ratio of 2-bromobutane to 1-bromobutane is very similar to the ratio of 2-chlorobutane to 1-chlorobutane. Can you offer and explanation as to why we do not observe the normal selectivity expected for bromination? Chlorine radicals perform the first propagation step (hydrogen abstraction) comparison to bromine radicals. Under these conditions in radicals form easily in the presence of chlorine radicals. Subsequently, the resulting radicals can react with bromine in a second propagation step to yield monobrominated products.arrow_forward11. See Fundamentals P167 for Figure 5.6 Use Figure 5.6 to rank the compounds in each of the following groups in order of their reactivity toward electrophilic aromatic substitution: (a) Nitrobenzene, phenol (hydroxybenzene), toluene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, aniline (aminobenzene)arrow_forwardParagraph 10. Answer ALL parts of this question. Treatment of acetylcyclopentane (see Scheme Q10a) with NaOEt in ethanol at 25 °C results in formation of a major, thermodynamic enolate (Scheme Q10a). NaOEt Thermodynamic enolate ELOH 25 °C (Scheme Q10a) (a) Draw the structure of the thermodynamic enolate. (b) Explain why the enolate in answer (a) is the major enolate present in the equilibrium at room temperature. (C) Draw the product formed when the thermodynamic enolate (1 mole) reacts with ethyl acrylate (1 mole) (Scheme Q10c). OEt + NaOEt Thermodynamic enolate Product ETOH 25 °C C12H2003 (Scheme Q10c) (d) Draw the kinetic product formed when 1-cyclopentene-1-carbaldehyde reacts with sodium cyanide at low temperature (5 °C) and over a short reaction time (5 minutes) (Scheme Q10d). NACN Kinetic product ELOH 5 °C (Scheme Q10d) >arrow_forward