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Under strongly acidic conditions, hexane is observed to undergo an isomerization process, during which it is converted into branched alkanes having the same molecular formula as hexane (C6H₁4). The rate at which each constitutional isomer is produced is related to the type of acid that is used in the reaction and the degree of mixing that occurs during the reaction (J. Chem. Soc., Perkins Trans. 2 1999, 12, 2715-2718). Step 1 Draw a bond-line structure of hexane. Draw Your Solution There are four branched isomers of hexane. Draw bond-line structures of all four of its isomers. Draw Your Solution

When 2-methylpropane is monochlorinated in the presence of light at room temperature, 36% of the product is 2-chloro-2-methylpropane and 64% is 1-chloro-2-methylpropane. From these data, calculate how much easier it is to remove a hydrogen atom from a tertiary carbon than from a primary carbon under these conditions.

Draw the structure of the major organic product(s) of the reaction. CH3 1. DIBAH, toluene + 2. H30* ChemDoodleⓇ DIBAH diisobutylaluminum hydride, [(CH3)2CHCH₂)2AIH • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu. D. n [F Previous

Provide the structure of the major organic products which result in the reaction below

Draw the structure of the major organic product(s) of the reaction. 1. LiAlH4, ether -CH3 2. H₂O • . You do not have to consider stereochemistry. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the

what is the product(s) of the reaction of p-bromoaniline with HNO2, H2SO4, then CuCl and HCl

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:

Predict the product of the following organic reaction: CH₂ CH O || C–CH2–CH=CH—(CH2)3 CH3 (CH₂)3 CH=CH- - CH₂ CH3 + 4 H₂ Ni CH,−O -C–CH2–CH=CH–CH=CH–CH2–CH3 Specifically, in the drawing area below, draw the chemical structure of the product P. If there is no product, because this reaction won't happen, check the No reaction box under the drawing area. Click and drag to start drawing a structure. × Ś +

Draw the structure(s) of the major organic product(s) of the following reaction. HO 1. Dry Et₂O + 1 eq. CH3CH2-Mgl 2. aqueous NH4Cl at 0° • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If the reaction produces a racemic mixture, draw both stereoisomers. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Include anionic counter-ions, e.g., I, in your answer, but draw them in their own sketcher. 2 ChemDoodle √n [

Shown below is a carbocation intermediate in an electrophilic addition reaction of HCl with an alkene. For the conformation shown, select each hydrogen whose bond to carbon is aligned for effective hyperconjugation with the vacant p orbital on the positively charged carbon. Each adjacent carbon will have only one C-H bond so aligned. • Gray = C; white = H; red = 0; blue = N; dark green = Cl; brown =Br; light green =F; purple = I; yellow = S; orange = P. • Double click to select atoms. • You can zoom in and out using the mouse scroll wheel (or pinch to zoom on touch screens).

Alkenes undergo an addition reaction with borane in tetrahydrofuran (THF). For the reaction below: BH3 THF (solvent) a Draw the structure of the major organic product. Use the wedge/hash bond tools to indicate stereochemistry where it exists. Use wedge and hash bonds ONLY when needed to show reaction stereochemistry. If the reaction produces a racemic mixture, just draw one stereoisomer. opy aste ChemDoodle

Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the major product. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If more than one structure fits the description, draw them all. • 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. ● VIL ? ChemDoodle Ⓡ Qt Sn [F

2. Draw structures for the following systems. If more than one isomer is possible, draw strcutures for all the possible isomers. Benzene ring with a methyl group and a nitro group (Draw all possible isomers, and name them) Benzene ring connected to a heptane chain (Draw all possible isomers, and name them) 2-benzyl-3- methylbutan-1-ol