Interpretation:
The reaction sequences involved in the conversion of the given reactant to products is to be sketched.
Concept introduction:
The grignard reagent or RMgX is a reagent that can be prepared from an
The organic reaction in which the conversion of an alkyl halide (primary or secondary) and a ketone or an aldehyde into an
Ethylene glycol protects carbonyl compounds by forming cyclic acetals.
Dienes react with dienophiles in high-temperature conditions to form cyclic products and the reaction is known as Diels Alder reaction.
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Chapter 16 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
- (a) Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBR3, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4-dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.arrow_forward4.33 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-Butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol (e) 1-Methylcyclopentanol or cyclohexanol Draw the energy diagrams of an SN1 reaction and an SN2 reaction. Include in your drawing anexample reaction. Identify the rate limiting step and label it as unimolecular or bimolecular.arrow_forwardAnswer Question a(i), a(ii), a(iii): a(iii) What reagents would be needed to prepare compound B from compound A and to convert compound B into C.arrow_forward
- Show how you might synthesize the following compounds, using acetylene and anysuitable alkyl halides as your starting materials. If the compound given cannot besynthesized by this method, explain why.(a) hex-1-yne (b) hex-2-ynearrow_forwardShow how you would use simple chemical tests to distinguish between the following pairs of compounds. In each case, describe what you would do and what you would observe. (a) butan-1-ol and butan-2-ol (b) butan-2-ol and 2-methylbutan-2-olarrow_forward5.34 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol dovolonentanol or cyclohexanolarrow_forward
- (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 NaOEtarrow_forwardUsing cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you haveshown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) cis-cyclooctene (b) cyclooctane (c) trans-1,2-dibromocyclooctanearrow_forwardUsing hex-1-ene as your starting material, show how you would synthesize the following compounds. (Once you haveshown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) 1,2-dibromohexanearrow_forward
- Predict the major product or the necessary reagent or reactant to complete each of the following reactions. In the box before each reaction, indicate the mechanism followed by the reaction. (Free radical (FR), SN2, SN1). (b) (a) Cl₂ CH₂CH₂OH (a) 1 hv 2 (b) H Br H₂O Na+ SCH3 (c) (d) CI "CH3arrow_forwardUsing cyclohexane as your starting material, show how you would synthesize each of the following compounds. (Onceyou have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) bromocyclohexane (b) cyclohexenearrow_forwardShow reagents to bring about each conversion. (c) Br (d) (b) (а) (e) (f) H.arrow_forward
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