Addition of HCI to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclo- hexane as the sole product. Use resonance structures to explain why none of the other regioisomer is formed.
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- 7.40 a. Suggest an explanation for the fact that 1-methylcyclopropene is some 42 kJ/mol (10 kcal/mol) less stable than methylenecyclopropane. -CH3 is less stable than CH2 1-Methylcyclopropene Methylenecyclopropane b. On the basis of your answer to part (a), compare the expected stability of 3-methylcyclopropene with that of 1-methylcyclopropene and that of methylenecyclopropane.The energy difference between cis- and trans-but-2-ene is about 4 kJ/mol; however, the trans isomer of 4,4-dimethylpent2-ene is nearly 16 kJ/mol more stable than the cis isomer. Explain this large difference.7Compounds X and Y are both C5H11CI products formed in the radical chlorination of pentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C5H10 alkene (ignoring double bond stereochemistry). Both X and Y react in SN2 fashion with sodium iodide in acetone; Y reacts faster than X. What is the structure of Y? • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodle (Previous Next
- cis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium ethoxide in ethanol to form 4-tert-butylcyclohexene. Explain why the cis isomer reacts much more rapidly than the trans isomer.Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis-and trans-1-bromo-3-methylcyclohexane and cis-and trans-1-bromo-2-methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1, 2-dibromocyclohexane as the soleproduct. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.Addition of HBr to allene (CH2=C=CH2) forms 2-bromoprop-1-ene ratherthan 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed froman allylic carbocation. Considering the arrangement of orbitals in theallene reactant, explain this result.
- 4.35 Formulate the reaction of cyclohexene with (i) Br2 and (ii) meta-chloro- peroxybenzoic acid followed by H30+. Show the reaction intermediates and the final products with correct cis or trans stereochemistry. 4.36 What products would you expect to obtain from reaction of cyclohexa- 1,3-diene with each of the following? (a) 1 mol Br2 in CH2C12 (c) 1 mol DCl (D = deuterium, ²H) (b) 1 mol HCl (d) 2 mol H2 over a Pd catalyst 4.37 Predict the products of the following reactions on hex-1-yne: (a) 1 equiv HBr ? (b) 1 equiv Cl2 ? (c) H2, Lindlar catalyst9.39. Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives which alkene? Account for the stereoselectivity of each 3-elimination. Me Me H Br Me Br Me Et Et Et Et (A) (В)-What of the following statements is false about cyclopentadienyl anion? A) It is aromatic B) It has 5 p molecular orbitals C) It has three full p bonding molecular orbitals D) It has one empty p anti-bonding molecular orbital E) It has two empty p anti-bonding molecular orbital 6. What is the correct IUPAC name of the following compound? A) 1-bromo-3-chloro-5-isobutyl-4-methylbenzene B) 5-bromo-1-chloro-3-sec-propyl-2-methylbenzene C) 5-bromo-1-sec-butyl-3-chloro-2-methylbenzene Br D) 1-bromo-3-sec-butyl-5-chloro-4-methylbenzene E) 5-bromo-1-chloro-3-isobutyl-2-methylbenzene II. Draw the structure for the major organic product of each of the following reaction: 7. CN + -> NC Show strerochemistry if necessary HBr 8. (1 equivalent) (45°C) Show strerochemistnu
- O PRACTICE PROBLEM 8.14 Starting with any needed alkene (or cycloalkene) and assuming you have deuterioace- tic acid (CH3CO,D) available, outline syntheses of the following deuterium-labeled compounds.s el en olad lo nohibbs ad CH3 (a) (CH3)2CHCH2CH,D (b) (CH3),CHCHDCH3 (c) (+ enantiomer) (d) Assuming you also have available BD3:THF and CH3CO2T, can you suggest a synthesis of the following? hab erl (+ enantiomer)he imo (nwond-ben) CH3 H. (asoholea)Compound A, C₂H16 reacts with 1 molar equivalent(s) of hydrogen on catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment, to give: O CH3 O || CH3CCH₂CCH₂CCH3 CH3 Compound A Propose a structure for A. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.2. Explain the selectivity of the following reaction, which produces a single product despite both alkene carbons being equally substituted. H3C CF3 HBr CF3 H3C CF3 H3C Br- H3C only product -H CF3