Chapter 10.6, Problem 15ATS

The cycloaddition of 2-methylfuran and the unsaturated lactam (see below) yields up to 4 regioisomeric and diastereomeric products, all chiral and racemic. + N-Ph CH3 a) Draw the structure of the 4 possible regio- and diastereomers of this reaction. b) Which compound will be the major product obtained? Explain your answer based on effects of primary and secondary orbital interactions. O 4 possible regio- and diastereomers 80 °C

Draw the major organic product formed by reaction of 2-hexyne with the following reagent: H₂O in H₂SO4 / HgSO4. • Consider E/Z stereochemistry of alkenes. • In cases where there is more than one answer, just draw one. • If no reaction occurs, draw the organic starting material.

A certain hydrocarbon had the molecular formula C16H26 and contained two triple bonds. Ozonolysis gave CH3(CH2), CO₂H and HO₂CCH2CH2CH2CH2CO₂H as the only products. Draw a reasonable structure for this hydrocarbon. Click and drag to start drawing a structure. D:

Review Topics] [References] Draw a structural formula for the major product of the reaction shown. CH;CH2 c=CHCH3 CH;CH2 Br2 H20 • Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer. Previous Next ChemDoodle Save and Ex tv ill I 11 МacBook Air DII DD F12 F11 F10 80 888 F9 F7 FB F6 F5 F4 F3 * & $ %3D 5 6. 7 8 9. 4 { P E R T Y H J K F + * CO

(dehydrobromination) A chemist carried out an elimination reaction of 1,1-dimethyl-2- bromocyclopentane. The chemist expected the reaction to yield alkene Z as product. However, alkene Z DID NOT form. Instead, three alkenes were produced: one alkene was the major product, the other two alkenes was the minor products. What was the major alkene product that formed? Br Select one: A. I B. II C. IV D. III alcohol HEAT || Z = + (HBr) IV

Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. CI H₂N OH • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na+, I, in your answer. • In cases where there is more than one answer, just draw one. Sn [F

Draw the cycloalkene that would react with the reagent given to account for the product formed. ? + H₂O H₂SO4 CH3 ▼ • 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. » [ ]# CH3 ? OH

A benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.

Allylic bromination of alkenes is accomplished with the reagent NBS (N-bromosuccinimide). The reaction proceeds by a radical chain mechanism. For the following reaction: NBS Br light, CCI4 a Select the species that you would expect to react in the first propagation step and draw curly arrows to show the mechanism. Use half-headed (fishhook) curved arrows to show electron reorganization. When drawing bond formation by pairing of single electrons, terminate the arrows in a hotspot located to one side of a reacting radical. This hotspot is not associated with any structural feature. Arrow-pushing Instructions 将一郎: Br H2 Previous Next