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:

Arrange the alkenes in each set in order of increasing rate of reaction with HI and explain the basis for your ranking. Draw the structural formula of the major product formed in each case.

CH3 OCH2CH2CH CH3 (10) (11) alkyl bromide/ phenyl bromide sodium alkoxide/ sodium phenoxide

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.

Mono-chlorination of n-butane yields 1-chlorobutane (30%) and 2- chlorobutane (70%). If each C-H bond had the same reactivity, the expected ratio of 1-chlorobutane to 2-chlorobutane would be: 30% : 70% 40% : 60% 50% 50% 60% : 40% 70% : 30%

-If (S)-2-bromo-3-methylbutane reacts with sodium methoxide (NaOCH) in a mixed solvent made from equal volume of methanol and hexane. The percent of the major product (enantiomer) if the reaction went to completion will be

As an example of a ver rare occurence, the following hydrocarbon reacts with two equivalents of butylithium to form a dianion of the formula [C8H6]2-  . Propose a structure for this dianion and explain why this dianion forms so readily.

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.