assignment 5 answers - CHM 1321 Assignment 5 Answers 1 Name...

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CHM 1321 Assignment 5 Answers 1) Name the following compounds a) b) c) d) e) f) g) 6-methylheptene or 6-methylhept-1-ene 2-ethylpentene or 2-ethylpent-1-ene 4-methylhepta-1,6-diene 4-vinylcyclohexene 3(S),4(R)-dimethylcyclopentene E -2-methyloct-4-ene 5Z -2,7-dimethylocta-1,5-diene 2) Predict the products of E1 elimination for the following compounds. Predict the relative amounts of each product. OH OH Br HOCH 3 a) b) c) H 2 SO 4 heat H 3 PO 4 heat OH + H + OH 2 H OH + H + OH 2 H H + H + + H + major (most substituted) minor (least substituted) HOCH 3 + H + HOCH 3 + HBr HOCH 3 + H + HOCH 3 + HBr major (most substituted) minor (least substituted) Br H
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Br HOC(CH 3 ) 3 d) HOC(CH 3 ) 3 + H + H HBr Major (most substituted) minor (least substituted) Br H HOC(CH 3 ) 3 HBr Br HOCH 3 Br HOCH 3 Br Br H H H H H HOCH 3 e) f) + + HBr + + HBr major (most substituted) minor (least substituted) + + HBr major (most substituted) + + HBr major (most substituted) + + HBr HOCH 3 HOCH 3 HOCH 3 HOCH 3 3) When 1-bromomethylcylcohexene is heated in ethanol, three products are observed. Give mechanisms to account for each product.
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Br Br HOCH 2 CH 3 H HOCH 2 CH 3 HOCH 2 CH 3 OCH 2 CH 3 H OCH 2 CH 3 H HOCH 2 CH 3 HOCH 2 CH 3 OCH 2 CH 3 OCH 2 CH 3 OCH 2 CH 3 OCH 2 CH 3 ethanol heat + + resonance hybrid + H 2 OCH 2 CH 3 + H 2 OCH 2 CH 3 + H 2 OCH 2 CH 3 4) The reaction of sodium ethoxide with methyl iodide is sensitive to the polarity of the solvent. Draw an energy diagram for this reaction in a protic solvent and in a dipolar aprotic solvent. Use the energy diagram to predict which reaction will be faster. H 3 C I + OCH 3 H H H IO C H 3 δ− δ− δδ+ O + I E reaction co-ordinate H 3 C I OCH 3 H H H C H 3 δ− δ− δδ+ O + I dipolar aprotic solvent protic solvent reaction in the dipolar aprotic solvent will be faster because the activation energy is lower in this solvent
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5) a) Design an alkyl halide that will give only 2, 4-diphenyl-2-pentene upon treatment with potassium tert-butoxide (a strong hindered base). Br placing the bromine at any other carbon is incorrect as this leads to 3 products Note: Cis/trans are still possible, but only one isomer will be obtained depending on the stereochemistry of the starting material (see parts below) Br ++
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assignment 5 answers - CHM 1321 Assignment 5 Answers 1 Name...

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