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- Compounds 1 and 2 were prepared, and the difference in their heats of combustion was found to be 17.2 kJ/mol (J. Am. Chem. Soc. 1961, 83, 606-614): H H 1 Shown below are the lowest-energy conformations of compounds 1 and 2. Identify which drawing matches which compound, and identify which compound has the larger heat of combustion. H H H H |||I 2 H 4 H H The first drawing is compound 1, and compound 1 has a larger heat of combustion because it is the less stable compound. O The first drawing is compound 2, and compound 2 has a larger heat of combustion because it is the less stable compound. The first drawing is compound 2, and compound 2 has a larger heat of combustion because it is the more stable compound. The first drawing is compound 1, and compound 1 has a larger heat of combustion because it is the more stable compound.3. Assign E or Z stereochemistry to the following alkenes: (a) НОСН2 CH3 (b) HO2C H C=C C=C H3C CI OCH3 (c) NC CH3 (d) CH3O2C CH=CH2 C=C C=C CH3CH2 CH2OH HO2C CH2CH3 4. Classify the following reactions as additions, eliminations, substitutions, or rearrangements: (а) CН3Br + KоН — СH3ОН + KBr (b) CH3CH2C1 + NaOH → (c) H2C=CH2 + H2 H2C=CH2 + NaCl CH3CH3 5. Which of the following are most likely to behave as electrophiles, and which as nucleophiles? Explain. (a) NH4+ (b) C=N- (c) Br+ (d) CH3NΗ, (е) Н—С—С-—нWhat is the structure of (1S.2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane? II OH IV
- (a) Draw all stereoisomers formed by monochlorination of the cis and trans isomers of 1,2-dimethylcyclobutane drawn below. (b) How many constitutional isomers are formed in each reaction? (c) Label any pairs of enantiomers formed.How's is 7-oxabicyclo[4.1.0]heptane converted to (1R,2S)-1,2-dimethylcyclohexaneThe bicyclic alkene P can be prepared by thermal electrocyclic ringclosure from cyclodecadiene Q or by photochemical electrocyclic ringclosure from cyclodecadiene R. Draw the structures of Q and R, andindicate the stereochemistry of the process by which each reactionoccurs.
- What is the correct answer and why?(a) Draw all stereoisomers formed by monobromination of the cis and trans isomers of 1,2-dimethylcyclohexane drawn below. (b) How do the products formed from each reactant compare-identical compounds, stereoisomers, or constitutional isomers? cis-1,2-dimethylcyclohexane trans-(1R.2S)-dimethylcyclohexane(1R,2R)-1-Bromo-2-methylcyclopentane is reacted with sodium methoxide. Given the product(s) and show the reaction mechanism, including the depiction of the transition state. Draw an energy diagram for this conversion.
- Identify the most stable conformation of trans-1-methyl-4-bromocyclohexane (5). A B Me (5) Me Br A Br B Me Br C Me Br Me DWrite the structures of Kand L, show exactly what happens in each reaction. Cycloocta triene 80-100°C cis,cis,cis-Cicloocta-1,3,5-trieno K (C;H10) COOCH3 A K + CH;00CC=CCOOCH, L (C,H1604) COOCH3 Ciclobuteno + Ftalato de dimetilo Ftalato de dimetilo dimethyl pht he laeteDetermine the double bond stereochemistry (E or Z) for the following molecules. F. H3C C A CH3 F. H B D Br