Summary of Reactions

To determine the product of oxidative cleavage, replace C=C withC=0 0=C. 

A ketone has two alkyl groups bonded to a carbonyl C=0 group an aldehyde has one hydrogen (or has two hydrogens) bonded to a carbonyl group. 

The heat of hydrogenation is the heat released in a hydrogenation reaction. It is the value without the negative sign. 

The most stable alkene has the smallest heat of hydrogenation. 

The stability of an alkene increases as the number of alkyl substituents bonded to its sp carbons increases. 

Alkenes are reduced by addition of H2 in the presence of a catalyst such as platinum or palladium to yield alkanes, a process called catalytic hydrogenation. Cis-l,2-diols can be made directly from alkenes by hydiroxyla-tion with OSO4. Alkenes can also be cleaved to produce carbonyl compounds by reaction with ozone, followed by reduction with zinc metal. 

Alkene polymers—large molecules resulting from repetitive bonding together of many hundreds or thousands of small monomer units—are formed by reaction of simple alkenes with a radical initiator at high temperature and pressure. Polj etbylene, polypropylene, and polystyrene are common examples. 

What s seven times nine Sixty-three, of course. You didn t have to stop and figure it out you knew the answer immediately because you long ago learned the multiplication tables. Learning the reactions of organic chemistry requires the same approach Reactions have to be learned for immediate recall if they are to he useful. 

Note No stereochemistry is implied unless specifically indicated with wedged, solid, and dashed lines. 

Markovnikov regiochemistry is observed H adds to the less highly substituted carbon, and X adds to the more highly substituted carbon. 

Alkenes are reduced by addition of H2 in the presence of a catalyst such as platinum or palladium to yield alkanes, a process called catalytic hydrogenation. Alkenes are also oxidized by reaction with a peroxyacid to give epoxides, which can be converted into trans-l,2-diols by acid-catalyzed hydrolysis. The corresponding cis-l,2-diols can be made directly from alkenes by hydroxylation with OSO4. Alkenes can also be cleaved to produce carbonyl compounds by reaction with ozone, followed by reduction with zinc metal. In addition, alkenes react with divalent substances called carbenes, R2C , to give cyclopropanes. Nonhalo-genated cyclopropanes are best prepared by treatment of the alkene with CH2I2 and zinc-copper, a process called the Simmons-Smith reaction. 

Many reactions give chiral products. If the reactants are optically inactive, the products are also optically inactive. If one or both of the reactants is optically active, the products can also be optically active. 

The chapter sections to review are shown after the name of the reaction. 

H— and —OH, bond to the carbon-carbon double bond to form an alcohol. 

The chapter section containing each Core Chemistry Skill is shown in 

Example a. Draw the condensed structural formula for 2-methyl-2-butene. 

1 Amines are substituted ammonia molecules and so have some similar properties. They are basic or alkaline compounds and their solutions have pHs above 7. Their base strength is expressed in terms of Aj, or pATb values. 

2 Amines react with acids to form salts. 

3 Ammonia can have its H atoms on the N progressively substituted by alkyl or aryl groups to form primary, secondary, tertiary and quaternary compounds. 

4 Amino acids have both an amino group and a carboxylic acid attached to the same carbon atom in the molecule. This carbon is amphoteric, and can accept protons like a base, or donate protons, like an acid. 

5 The H on the N of the amine group can also be substituted by other groups especially by acyl groups such as COCH3, when attacked by ethanoyl chloride, CH3COCI or ethanoic anhydride, (CH3C0)20. 

Markovnikov regiochemistry occurs, w ith H adding to the less highly substituted alkene carbon and halogen adding to the mote highly substituted carbon. 

Anti addition is observed through a halonium ion intermediate 

Thomson- - Vv Sign in at www.fhomsonedu.com to assess your knowledge of this chapter s topics by taking a pre test. The pre-test will link you to interactive organic chemistry resources based on your score in each concept area. 

Example For the following redox reaction, identify the reactant that is oxidized, and the reactant that is reduced  

Example. Assign oxidation numbers to each of the elements in the following  

Example Assign oxidation numbers to each element and identify which is oxidized and which is reduced. 

Example Identify the oxidizing agent and the reducing agent in the following  

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Summary of Reactions Discussed in Earlier Chapters That Yield Alcohols... 

Summary of Reactions of Alcohols Discussed in Earlier Chapters... 

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