Unit C—Chemical Changes of Organic Compounds

General Outcome 1: Students will explore organic compounds as a common form of matter

Knowledge30–C1.1k Define organic compounds as compounds containing carbon, recognizing inorganic exceptions such as carbonates, cyanides, carbides and oxides of carbon.

The compounds numbered above that can be classified as organic are _____, _____, _____, and _____.

The compounds numbered above that can be classified as organic are _____, _____, _____, and _____.

Which of the following chemical compounds is not considered an organic compound?A. C2H5COOCH3(l)B. C6H5COOH(s)C. CH3CH2OH(l)D. NH4CN(s)

The chemical compounds numbered above that represent organic compounds are _____, _____, _____, and _____.

Knowledge30–C1.2k Identify and describe significant organic compounds in daily life, demonstrating generalized knowledge of their origins and applications; e.g., methane, methanol, ethane, ethanol, ethanoic acid, propane, benzene, octane, glucose, polyethylene.

Knowledge30–C1.3k Name and draw structural, condensed structural and line diagrams and formulas, using International Union of Pure and Applied Chemistry (IUPAC) nomenclature guidelines, for saturated and unsaturated aliphatic (including cyclic) and aromatic carbon compounds.

The molecular formula for 2,5-dimethylcyclohexan-1-ol is A. C6H6O B. C6H12O C. C8H13O D. C8H16O

Cycloheptane is i hydrocarbon, and cycloheptene is ii hydrocarbon. The statement above is completed by the information in row

Row i iiA. a saturated a saturatedB. a saturated an

unsaturatedC. an

unsaturateda saturated

D. an unsaturated

an unsaturated

The IUPAC name for the structural diagram the student drew is 1- i -2- ii . The statement above is completed by the information in row

Row i iiA. methyl ethylbutaneB. methyl ethylcyclobutan

eC. ethyl methylbutaneD. ethyl methylcyclobut

ane

The structural diagram that represents CH3C(CH3)2CH3 is

The IUPAC name for the structural diagram above isA. 2,2,5-trimethylheptaneB. 3,6,6-trimethylheptaneC. 2-ethyl-5,5-dimethylhexaneD. 5-ethyl-2,2-dimethylhexane

The IUPAC name for the structural diagram the student drew is 1- i -2- ii . The statement above is completed by the information in row

Row i ii

A. methyl propylbutaneB. methyl propylcyclobutan

eC. propyl methylbutaneD. propyl methylcyclobutan

e

Which of the following line diagrams represents 2,2,4-trimethylpentane?

Which of the following rows identifies the structural diagram and the corresponding IUPAC name of the compound with the chemical formula C8H16(l)?

An interpretation that could be made from the student’s observation is that the hydrocarbon sample is i and the IUPAC name of the sample could be ii . The statement above is completed by the information in rowRow i iiA. saturated hex-2-eneB. saturated cyclopentaneC. unsaturated hex-2-eneD. unsaturated cyclopentane

Ethene can be described as both an i compound and ii molecule. The statement above is completed by the information in row

Row i iiA. aliphatic a saturatedB. aliphatic an

unsaturatedC. aromatic a saturatedD. aromatic an

unsaturated

Knowledge30–C1.4k Identify types of compounds from the hydroxyl, carboxyl, ester linkage, and halogen functional groups, given the structural formula.

An ester functional group is found in A. II and III only B. II, III, and IV C. III only D. IV only

The organic compound numbered above that is an alkene is __________ (Record in the first column) is an alcohol is __________ (Record in the second column) contains a triple bond is __________ (Record in the third column) is cyclic and saturated is __________ (Record in the fourth column

Match four of the organic compounds numbered above with their classifications below. Alkyne __________ (Record in the first column)

Alcohol __________ (Record in the second column) Aromatic __________ (Record in the third column) Unsaturated hydrocarbon __________ (Record in the fourth column)

Butanoic acid can be described as an i compound, and the functional group in butanoic acid is ii .

The statement above is completed by the information in rowRow i iiA. aromatic a carboxylB. aromatic an esterC. aliphatic a carboxyl

D. aliphatic an ester

Match the structural diagrams above with their classifications given below. Alcohol __________ (Record in the first column) Aromatic __________ (Record in the second column) Carboxylic acid __________ (Record in the third column) Halogenated hydrocarbon __________ (Record in the fourth column)

The organic compound numbered above that is an alkene is __________ (Record in the first column) is an alcohol is __________ (Record in the second column) contains a triple bond is __________ (Record in the third column) is cyclic and saturated is __________ (Record in the fourth column)

Match each of the structural diagrams above with its classification below. Aromatic __________ (Record in the first column) Carboxylic acid __________ (Record in the second column) Unsaturated and aliphatic __________ (Record in the third column) Halogenated hydrocarbon __________ (Record in the fourth column)

Match the general structural diagrams numbered above with the class of the compound below.Carboxylic acid __________(Record in the first column)Aromatic __________ (Record in the second column)Alcohol __________(Record in the third column)Ester __________(Record in the fourth column)

The structures and descriptions above that apply to methylcyclopentane are numbered_____,_____,_____ , and_____.

An ester functional group is found in A. II and III only B. II, III, and IV C. III only D. V only

The structural diagram above represents an___ i___ compound that contains a ___ii___ and an ___iii___ functional group. The statement above is completed by the information in row

Knowledge30–C1.5k Define structural isomerism as compounds having the same empirical formulas, but with different structural formulas, and relate the structures to variations in the properties of the isomers.

The four molecules listed above that are isomers of C5H10(l) are numbered _____, _____, _____, and ______.

Which of the structural diagrams numbered above represent isomers?A. I and IIB. I and IVC. II and IIID. III and IV

Which of the following rows identifies the condensed structural diagram or line diagram and the IUPAC name of an isomer of C6H12?

Knowledge30–C1.6k Compare, both within a homologous series and among compounds with different functional groups, the boiling points and solubility of examples of aliphatics, aromatics, alcohols, and carboxylic acids.

Listed in order from the acid that has the lowest boiling point to the acid that has the highest boiling point, the four organic acids above are numbered

________, ________, ________, and ________.Lowest boiling point Highest boiling point

Which of the following structural diagrams represents the compound with the lowest boiling point?

Knowledge30–C1.7k Describe, in general terms, the physical, chemical and technological processes (fractional distillation and solvent extraction) used to separate organic compounds from natural mixtures or solutions; e.g., petroleum refining, bitumen recovery

The method of separating the mixture of hydrocarbon compounds in crude oil that is represented in the diagram above isA. titration B. precipitation C. solvent extractionD. fractional distillation

A mixture of liquid methanol and liquid ethanol can be separated by i , and the physical characteristic of these compounds that allows the separation is ii . The statement above is completed by the information in row

Row i iiA. fractional

distillationsolubility

B. fractional distillation

boiling point

C. precipitation solubilityD. precipitation boiling point

General Outcome 2: Students will describe chemical reactions of organic compounds

Knowledge30–C2.1k Define, illustrate, and provide examples of simple addition, substitution, elimination, esterification and combustion reactions.

Match each equation representing the reactions numbered above with the type of reaction it exemplifies below. Addition __________(Record in the first column)Substitution __________ (Record in the second column)Elimination __________(Record in the third column)Esterificaton __________(Record in the fourth column)

The production of propan-2-ol from propene is i reaction. Propan-2-ol is likely to be ii in water.

The statement above is completed by the information in rowRow i iiA. a substitution solubleB. a substitution insolubleC. an addition solubleD. an addition insoluble

Knowledge30–C2.2k Predict products and write and interpret balanced equations for simple addition, substitution, elimination, esterification and combustion reactions.

The reactants above undergo an i reaction, and the product of the reaction is 1,2-dibromo ii .

The statement above is completed by the information in rowRow i iiA. elimination ethaneB. elimination etheneC. addition ethaneD. addition ethene

Hexane is i hydrocarbon, and hex-1-ene is ii hydrocarbon. The statement above is completed by the information in row

Row i iiA. a saturated a saturatedB. a saturated an

unsaturatedC. an

unsaturateda saturated

D. an unsaturated

an unsaturated

When aqueous bromine is added to hexane and hex-1-ene in the presence of light, the hexane undergoes i reaction and the hex-1-ene undergoes ii reaction. The statement above is completed by the information in row

Row i iiA. an addition a substitutionB. an addition an additionC. a substitution a substitutionD. a substitution an addition

When methanol and ethanoic acid react, the products areA. ethyl methanoate only

B. methyl ethanoate onlyC. ethyl methanoate and waterD. methyl ethanoate and water

When aqueous bromine is added to cycloheptane and cycloheptene, the cycloheptane undergoes i reaction, and the cycloheptene undergoes ii reaction. The statement above is completed by the information in row

Row i iiA. an addition a substitutionB. an addition an additionC. a substitution a substitutionD. a substitution an addition

The type of reaction that occurs when ethene gas and chlorine gas react is ___i___ , and the name of the organic compound produced is ___ii___ .The statement above is completed by the information in rowRow i iiA. addition 1,2-dichloroethaneB. addition 1-chloroetheneC. substitution 1,2-dichloroethaneD. substitution 1-chloroethene

Match a name or a term from the list above with each descriptor given below. Name of reactant I __________ (Record in the first column) Name of product II __________ (Record in the second column) Type of reaction __________ (Record in the third column) Classification of product II __________ (Record in the fourth column)

The ester shown above could be produced by the reaction of i and ii . The statement above is completed by the information in row

Row i iiA. ethanoic acid pentan-1-olB. ethanoic acid butan-1-olC. pentanoic

acidpropan-1-ol

D. pentanoic acid

ethanol

Match a name or a term from the list above with each descriptor given below. Type of reaction __________ (Record in the first column) Name of compound I __________ (Record in the second column) Name of compound II __________ (Record in the third column) Classification of compound II __________ (Record in the fourth column)

Match the reactants and type of reaction numbered above with two of the methods of producing chloroethane below.

Knowledge 30–C2.3k Define, illustrate, and provide examples of monomers (e.g., ethylene), polymers (e.g., polyethylene) and polymerization in living systems (e.g., carbohydrates, proteins) and nonliving systems (e.g., nylon, polyester, plastics).

Which of the following rows identifies a reactant and its product in a polymerization reaction?Row Reactant ProductA. Ethene EtheneB. Ethene PolyetheneC. Propen

eEthene

D. Propene

Polyethene

Match the IUPAC name or the organic term numbered above with its descriptor below. Product name __________(Record in the first column)Reactant name ___________(Record in the second column)Type of organic reaction __________(Record in the third column)Classification of product __________ (Record in the fourth column)

Which of the following monomers is required to produce the polymer in the structural diagram above?A. CH2–Cl–CH2–ClB. CH3–CH2–ClC. CH2=CHClD. CH=CCl

Knowledge 30–C2.4k Relate simple addition, substitution, elimination, esterification and combustion reactions to major reactions that produce thermal energy and economically important compounds from fossil fuels.

During this___i___ reaction, energy is___ii___ the surroundings. The statement above is completed by the information in rowRow i iiA. combustion released toB. combustion absorbed fromC. elimination released toD. elimination absorbed from