What is the expected integration of the vinylic hydrogens (hydrogens attached to carbons of a C=C bond) in each product? 2-methyl-1-butene: 2-methyl-2-butene:

Explain the fact that the C-O stretch in ethers and esters occurs at 1000-1100 cm-1 when the C is sp hybridized, but at 1250 cm- when it is sp2 hybridized.

Which of these alkyl chlorides undergoes dehydrohalogenation in the presence of a strong base to give pent-2-ene (shown below) as the only alkene product? O l-chloro-2-methylbutane O 2-chloropentane O 3-chloropentane O 1-chloropentane O l-chloro-3-methylbutane

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.

Compound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10: Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst to give z (C14H14) and reacts with ozone to give one product, benzoic acid (C,Hg02). Draw the structure of compound Z. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Ignore alkene stereochemistry. • 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. ChemDoodle

Explain why heats of hydrogenation cannot be used to determine the relative stability of 2-methylpent-2-ene and 3-methylpent-1-ene. A, B, and C, each subjected to hydrogenation. The number of rings and π bonds refers to the reactant (A, B, or C) prior to hydrogenation.

Draw the line-angle formula of the enol formed in the following alkyne hydration reaction and then draw the structural formula of the carbonyl compound with which this enol is in equilibrium. -C=CH 1. (sia)2BH 2. NaOH/H₂O₂ an enol carbonyl compound • You do not have to consider stereochemistry. • Draw both the enol and the carbonyl forms. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures using the sign from the drop-down menu. ChemDoodleⓇ <

Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.

Carbons 1 and 4 of 1,3-cyclohexadiene are equivalent (they form the same carbocation upon protonation.) Likewise, carbons 2 and 3 are also equivalent. Draw the bond-line formula (or skeletal structure) of the carbocation formed by protonation of C-2 or C-3 to verify that it is not allylic and therefore not a stable as the one formed by protonation of C-1 or C-4.

Which will yield 2-methylpentane upon catalytic hydrogenation?