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:

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

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%

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.

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Ⓡ <

Organic chemistry

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.

Which will yield 2-methylpentane upon catalytic hydrogenation?

Below is a mechanism that represents the following single reaction sequence: a certain alcohol undergoes acid- catalyzed dehydration (conversion that involves the loss of water from the reacting molecule or ion) to form an alkene product. Write the IUPAC name of the product. Include E/Z stereochemistry.       Hint: Name of the substituent of the product is similar to that of reactant.