01:160:307 Lecture Notes - Lecture 6: Bond Energy, Alkene, Abscissa And Ordinate

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1 May 2018

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Chemical Reactions – Mechanism

In a chemical reaction a starting material (or materials), SM, is (or are) converted to a product (or

products), P.

SM P

We will encounter many different reaction types.

A B rearrangement

A + B C addition

A + B C + D substitution, elimination

A B + C fragmentation

So far in this course, you have learned about one relatively simple reaction type, the transfer of a

proton, H+, from an acid to a base. Beginning with the second chapter on alkenes we will learn

many more reactions, both simple and complicated. Each of these reactions has three aspects that

we need to understand: its kinetics, its energetics, and its mechanism.

We will ask three questions about each reaction – the answers are provided by these approaches

How fast is the conversion? KINETICS

Is there a change in energy? THERMODYNAMICS ENERGEICS

How are the individual atoms disconnected and reconnected? MECHANISM

Kinetics: The rate at which the starting material, SM, is depleted and the rate at which the

product, P, is being formed. In this course kinetics will be introduced in detail in Chapter 9, but

we will describe and compare some simple kinetic aspects like fast (faster) or slow (slower).

Energetics: The changes in free energy and enthalpy as the starting material(s), SM, is (are)

converted to the product(s), P. We will discuss energetics to some extent.

Mechanism: the detailed description of how the structure(s) of the starting material(s), SM, is

(are) converted to the structure(s) of the product(s), P.

The starting material(s) has (have): a

composition (the number of each type of

atom present); a structure(s), i.e., which

atoms are connected to which, bond lengths,

bond strengths, and bond angles, dihedral

angles; a characteristic energy.

The product(s) MUST have the same

composition as the starting material(s)

[you cannot lose or gain any atoms – the two

sides are balanced in composition and

charge]; the structure (connectivity) has

changed; the energy !may change, too.

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Document Summary

In a chemical reaction a starting material (or materials), sm, is (or are) converted to a product (or products), p. B + c rearrangement addition substitution, elimination fragmentation. The starting material(s) has (have): a composition (the number of each type of atom present); a structure(s), i. e. , which atoms are connected to which, bond lengths, bond strengths, and bond angles, dihedral angles; a characteristic energy. The product(s) must have the same composition as the starting material(s) [you cannot lose or gain any atoms the two sides are balanced in composition and charge]; the structure (connectivity) has changed; the energy may change, too. So far in this course, you have learned about one relatively simple reaction type, the transfer of a proton, h+, from an acid to a base. Beginning with the second chapter on alkenes we will learn many more reactions, both simple and complicated.

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11/3 11/4 4 (a) What is an a-amino acid? (b) How do amino acids react to form proteins? Vinyl chloride is industrially important because it is the monomer from which the polymer, poly(vinyl chlonide (PVC) is obtained. Explain what s meant by monomer and polymer and name the process by which a monomer is converted to a polymer Wite an equation to represent the conversion of vinyl chloride to PVC 5 Write a chemical equation for the formation of alanylserine from the constituent amino acids 10. Polypeptides and proteins are important biological examples of condensation polymers. Draw in 2-D, two repeating units of the polypeptide formed only from the amino acid, glycine: NH CH-CO,H 6 Wha t amino acids would be obtained by hydrolysis of the following tripeptide? H2NCHCNHCH CNHCHCOH 11. Nylon is a polyamide-type of polymer often derived from the reaction between two different monomers 1,6-diaminohexane, HN(CHzuNH, and hexane 1,6-dioic acid HOC(CH2)aCO2H. (CHj)2 ?? ????? ?? (a) Identify electrophilic and nucleophilic sites in each of the reactant molecules and then indicate which atoms are likely to react with each other Given that one water molecule is eliminated for each reaction between two monomer molecules give a part structure of the polymer comprising three monomer units Polymers 7. What is the difference between a monomer and a polymer? (b) 8. Clearly define: (a) addition polymers (b) condensation polymers 9 Chloroethene (rinyl chloride) CHa CHCI, is an important industrial organic chemical. In industry it is produced by two different reaction sequences. (a) One reaction sequence involves reaction between ethene (ethylene) and chlorine, followed by strong heating of the reaction product. Write equations to represent these two reactions and classify each reaction as either substitution, addition or elimination. (b) The other reaction uses ethyne (acetylene) as the organic starting material. Write an equation to represent the reaction by which ethyne can be converted to vinyl chloride

Show transcribed image text 11/3 11/4 4 (a) What is an a-amino acid? (b) How do amino acids react to form proteins? Vinyl chloride is industrially important because it is the monomer from which the polymer, poly(vinyl chlonide (PVC) is obtained. Explain what s meant by monomer and polymer and name the process by which a monomer is converted to a polymer Wite an equation to represent the conversion of vinyl chloride to PVC 5 Write a chemical equation for the formation of alanylserine from the constituent amino acids 10. Polypeptides and proteins are important biological examples of condensation polymers. Draw in 2-D, two repeating units of the polypeptide formed only from the amino acid, glycine: NH CH-CO,H 6 Wha t amino acids would be obtained by hydrolysis of the following tripeptide? H2NCHCNHCH CNHCHCOH 11. Nylon is a polyamide-type of polymer often derived from the reaction between two different monomers 1,6-diaminohexane, HN(CHzuNH, and hexane 1,6-dioic acid HOC(CH2)aCO2H. (CHj)2 ?? ????? ?? (a) Identify electrophilic and nucleophilic sites in each of the reactant molecules and then indicate which atoms are likely to react with each other Given that one water molecule is eliminated for each reaction between two monomer molecules give a part structure of the polymer comprising three monomer units Polymers 7. What is the difference between a monomer and a polymer? (b) 8. Clearly define: (a) addition polymers (b) condensation polymers 9 Chloroethene (rinyl chloride) CHa CHCI, is an important industrial organic chemical. In industry it is produced by two different reaction sequences. (a) One reaction sequence involves reaction between ethene (ethylene) and chlorine, followed by strong heating of the reaction product. Write equations to represent these two reactions and classify each reaction as either substitution, addition or elimination. (b) The other reaction uses ethyne (acetylene) as the organic starting material. Write an equation to represent the reaction by which ethyne can be converted to vinyl chloride

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For each of the following, fill in the blank with the correct response. All of these fill-in-the-blank problems pertain to material covered in the sections on alkanes, alkenes and alkynes, aromatic hydrocarbons, and hydrocarbon derivatives.

a. The first "organic" compound to be synthesized in the laboratory, rather than being isolated from nature, was _ _ _ _ _, which was prepared from _ _ _ _ _.

b. An organic compound whose carbon-carbon bonds are all single bonds is said to be _ _ _ _ _.

c. The general orientation of the four pairs of electrons around the carbon atoms in alkanes is _ _ _ _ _.

d. Alkanes in which the carbon atoms form a single unbranched chain are said to be _ _ _ _ _ alkanes.

e. Structural isomerism occurs when two molecules have the same number of each type of atom but exhibit a different arrangement of the _ _ _ _ _ between those atoms.

f. The systematic names of all saturated hydrocarbons have the ending _ _ _ _ _ added to a root name that indicates the number of carbon atoms in the molecule.

g. For branched hydrocarbon, the root name for the hydrocarbon comes from the number of carbon atoms in the _ _ _ _ _ continuous chain in the molecule.

h. The positions of substituents along the hydrocarbon framework of a molecule are indicated by the _ _ _ _ _ of the carbon atom to which the substituents are attached.

i. The major use of alkanes has been in _ _ _ _ _ reactions, as a source of heat and light.

j. With very reactive agents, such as the halogen elements, alkanes undergo _ _ _ _ _ reactions, whereby a new atom replaces one or more hydrogen atoms of the alkane.

k. Alkenes and alkynes are characterized by their ability to undergo rapid, complete _ _ _ _ _ reactions, by which other atoms attach themselves to the carbon atoms of the double or triple bond.

l. Unsaturated fats may be converted to saturated fats by the process of _ _ _ _ _.

m. Benzene is the parent member of the group of hydrocarbons called _ _ _ _ _ hydrocarbons.

n. An atom or group of atoms that imparts new and characteristic properties to an organic molecule is called a _ _ _ _ _ group.

o. A _ _ _ _ _ alcohol is one in which there is only one hydrocarbon group attached to the carbon atom holding the hydroxyl group.

p. The simplest alcohol, methanol, prepared industrially by the hydrogenation of _ _ _ _ _.

q. Ethanol is commonly prepared by the _ _ _ _ _ of certain sugars by yeast.

r. Both aldehydes and ketones contain the _ _ _ _ _ group, but they differ in where this group occurs along the hydrocarbon chain.

s. Aldehydes and ketones can be prepared by _ _ _ _ _ of the corresponding alcohol.

t. Organic acids, which contain the _ _ _ _ _ group, are typically weak acids.

u. The typical sweet-smelling compounds called _ _ _ _ _ result from the condensation reaction of organic acid with an _ _ _ _ _.

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01:160:307 Lecture Notes - Lecture 6: Bond Energy, Alkene, Abscissa And Ordinate

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