History of Organic Chemistry
History of Organic Chemistry
The first organic chemical to be synthesized in a lab from inorganic chemicals was
a. ethanol c. methane
b. sugar d. urea
The first person to synthesis an organic chemical from inorganic chemicals was
a. August Kekulé c. Friedrich Wöhler
b. John Dalton d. Raymond LeMieux
The Avitalism@ theory in organic chemistry held that
a. organic chemicals can only be obtained from living organisms
b. organic chemicals can only be obtained from dead organisms
c. organic chemicals can only be obtained from living or dead organisms
d. organic chemicals can be obtained from any source of chemicals, organic or inorganic.
Long Answer:
Explain why Wöhlers synthesis of urea by heating ammonium cyanate crystals was a landmark event in the study of organic compounds.
Definition of Organic Chemistry
Organic chemicals
a. are all the compounds of carbon including the ionic compounds
b. are all the molecular compounds of carbon except the oxides
c. are all the ionic compounds of carbon including the oxides
d. can only be made by living organisms
Throughout history there have been many definitions of organic chemistry. The modern definition of organic chemistry refers to the study of
a. ionic compounds of carbon
b. molecular compounds of carbon
c. non-living substances only
d. substances derived from living things.
Which is an organic chemical?
a. CaCO3 c. Cl2
b. CCl4 d. CO2
Which is NOT an organic chemical?
a. CH3COOH c. C4H7O
b. CO2 d. CCl4
Which is NOT an organic chemical?
c. CH3CHO c. C2H6O
d. CBr4 d. CO
Which substance is organic?
a. AgCl c. NH4CN
b. AgOCN d. (NH2)2CO
Multitude of Organic Chemicals
Which statement is true?
a. Carbon can bond in chains with branches, but cannot form rings
b. Carbon can form single bonds, but not double and triple bonds.
c. Carbon can bond in chains with branches, in rings, and with single, double and triple bonds
d. Carbon cannot form rings with double bonds or branches on them
Which statement is true?
a. Over 90% of all known compounds are organic
b. Over 90% of all known compounds are inorganic
c. There are about 2 times as many inorganic compounds as organic compounds
d. There are about 2 times as many organic compounds as organic compounds
There are thousands of times more organic than inorganic compounds. The enormous number of carbon compounds is believed to be due, in large part, to the
a. high bonding capacity of a carbon atom.
b. ability of carbon atoms to form covalent bonds with hydrogen.
c. high number of lone pairs of electrons of a carbon atom.
d. large variety of chemical reactions of elemental carbon
Short Answer:
List three factors that contribute to the tremendous diversity of carbon compounds relative to the number of inorganic compounds.
Give two (good) reasons why carbon has its own branch of chemistry.
Homologous Series
Each member of the alkane series differs from the preceding member by one additional carbon atom and
a. 1 hydrogen atom c. 2 hydrogen atoms
b. 3 hydrogen atoms d. 4 hydrogen atom
The alkane family is referred to as a homologous series because each member of the family
a. becomes more soluble in water as they get larger
b. can have more isomers as they get larger
c. has a boiling point that increases as they get larger
d. increases by A-CH2" as they get larger
Which of the following is part of a homologous series:
a. CH4, C2H4, C4H8 b. CH4, C2H2, C3H6
c. C3H8, C3H6, C3H4 d. C2H4, C3H6, C4H8
Which term describes this group of compounds?
chloromethane, chloroethane, 1-chloropropane, 1-chlorobutane
a. aldehydes c. functional isomers
b. aromatics d. homologous series
Alkanes/Straight chain alkanes
Alkanes are:
a. organic compounds containing one or more carbon-carbon double bonds
b. special group of unsaturated cyclic hydrocarbons
c. organic compounds containing one or more carbon-carbon triple bonds
d. hydrocarbons that contain only single covalent bonds
How many double covalent bonds are in an alkane?
a. none c. one
b. two d. The number varies
How many carbons are in a molecule of hexane?
a. 3 b. 4
b. 5 d. 6
What is the name of the alkane having five carbons?
a. hexane c. methane
b. octane d. pentane
What increment of change occurs between propane and butane in the alkane series?
B
a. -CH- b. -CH2-
b. -CH3- d. -CH2=
Which of the following is a condensed structural diagram for propane?
a. C3H8
b. CH3-CH2-CH3 d.
c. C-C-C
What is the name of the molecule on the right?
a. butane
b. pentane
c. propane
d. tetrane
What is the name of the molecule on the right?
a. butane
b. pentane
c. propane
d. hexane
What is the IUPAC name of the compound on the right?
a. butane
b. decane
c. propane
d. pentane
What is the name of the straight chain alkane with 7 carbons?
a. pentane c. hexene
b. heptane d. octyne
Branched Alkanes - Nomenclature
Which condensed structural formula represents the alkyl group called ethyl?
a. CHCH c. CH2CH3
b. CH2CH2 d. CH3CH3
What is the name of an alkyl group that contains two carbon atoms?
a. diphenyl c. dimethyl
b. ethyl d. propyl
What prefix is used to represent the substituent CH3-CH2-CH2-?
a. ethyl- c. methyl-
b. propyl- d. pentyl
If a substituent appears four times in an organic compound, what prefix is used?
a. di- c. mono-
b. penta- d. tetra-
What is the name of the compound on the right?
a. 2,4-diethyl-2-methylhexane
b. 3-ethyl-5,5-dimethylheptane
c. 5-ethyl-3,3-dimethylheptane
d. 3,5-diethyl-5-methylhexane
What is the IUPAC name of compound on the right?
a. 2-ethyl-3-dimethylhexane
b. 2-ethyl-3,3-diemethylhexane
c. 4,4,5-trimethylheptane
d. 3,4,4-trimethylheptane
What is the IUPAC name of compound on the right?
a. 2,3-dimethylpentane
b. 3,4-dimethylpentane
c. 3,4,4 -trimethylbutane
d. 2,3,4-trimethylbutane
What is the IUPAC name of compound on the right?
a. trimethylpentane
b. 2-methyl-3-methyl-4-methylpentane
c. 2,2-dimethyl-3-methylpentane
d. 2,3,4-trimethylpentane
What is the IUPAC name of compound on the right?
a. 2-ethyl-2,4,5-trimethylpentane
b. 2-ethyl-2,4-dimethylhexane
c. 3,5,5-trimethylheptane
d. 3,3,5-trimethylheptane
What is the correct IUPAC name for the compound shown below? CH3.CH(CH2.CH3).CH(CH3)2
a. 2,3-dimethyl pentane c. 1,1,2-trimethyl butane
b. 2-ethyl-3-methyl butane d. 3,4-dimethyl pentane
Which is the condensed structural formula for 2,2,3-trimethylbutane?
a. CH3CH2(CH3)CH(CH3)2 c. CH3C(CH3)2C(CH3)3
b. CH3C(CH3)2CH(CH3)2 d. CH3CH2CH(CH3)C(CH3)3
What is the IUPAC name for this compound? CH3CH(CH3)C(CH3)3.
a. 2,2,3-trimethylbutane c. tetramethylpropane
b. 1,1,1,2-tetramethylpropane d. heptane
Alkenes - Nomenclature
Alkenes are:
a. organic compounds containing one or more carbon-carbon double bonds
b. special group of unsaturated cyclic hydrocarbons
c. organic compounds containing one or more carbon-carbon triple bonds
d. hydrocarbons that contain only single covalent bonds
Which hydrocarbon contains a double carbon to carbon bond?
a. 1-butene c. 2-methylbutane
b. 1-butyne d. cyclobutane
Which compound is an alkene?
a. butyne c. pentane
b. nonene d. propanone
What is the name of the molecule on the right?
a. 2-ethyl-3-propyl-1-pentene
b. 2,3-diethyl-4-methyl-1-pentene
c. 3-ethyl-2,4-dimethyl4-hexene
d. 3,4-diethyl-2-methyl-4-pentene
What is the name of the molecule on the right?
a. 2,3-dimethyl-4-propyl-4-pentene
b. 2,3-dipropyl-1-butene
c. 3,4-dimethyl-2-propyl-1-pentene
d. 4,5,6-trimethyl-4-heptene
What is the IUPAC name of this compound?
a. 1,1-dimethyl-2-butene
b. 2-methyl-3-pentene
c. 4-methyl-2-pentene
d. methylhexane
According to the rules established by chemists, what is the IUPAC name of the compound on the right?
a. 1-methyl-1-pentene
b. 5-methyl-4-pentene
c. 2,3-hexene
d. 2-hexene.
Determine the IUPAC name for the following molecule:
a. 2,5-dimethyl-2-hexene
b. 2,5-dimethyl-4-hexene
c. 2,5-dimethyl-2-heptene
d. 2,5-dimethyl-4-heptene
What is the name for the following molecule?
a. 2-ethyl-2-pentene
b. 4-ethyl-3-pentene
c. 3-methyl-3-hexene
d. 4-methyl-3-hexene
The correct name for the compound (CH3)2CH.CH(CH3).CH2.CH:CH2 is:
a. 4,5,5-trimethyl-1-pentene b. 4,5-dimethyl-1-hexene
c. 2,3-dimethyl-5-hexene d. 4-propyl-4-methyl-1-butene
Alkynes - Nomenclature
Alkynes are:
a. organic compounds containing one or more carbon-carbon double bonds
b. special group of unsaturated cyclic hydrocarbons
c. organic compounds containing one or more carbon-carbon triple bonds
d. hydrocarbons that contain only single covalent bonds
What is the name of the smallest alkyne?
a. butyne c. ethyne
b. methyne d. propyne
What is the name of the molecule on the right?
a. 4,4-diethyl-2-butyne
b. 4-ethyl-2-hexyne
c. 3-ethyl-4-hexyne
d. 1,1-diethyl-2-butyne
What is the name of the molecule on the right?
a. 1,6,6,6-tetramethyl-2-pentyne
b. 2,2-dimethyl-4-heptyne
c. 2,2,6-trimethyl-4-hexyne
d. 6,6-dimethyl-3-heptyne
Which is the condensed structural diagram for 4-methyl-2-pentyne?
a. [pic] c. [pic]
b. [pic] d. [pic]
What is the name of the molecule [pic] ?
a. acetylene c. propyne
b. 1-butyne d. propene
Cycloalkanes, cylcoalkene - Nomenclature
What is the name of the molecule on the right?
a. ethylbenzene
b. ethylcyclohexane
c. phenylethane
d. propylcyclohexane
What is the name of the molecule on the right?
a. butylcyclohexane
b. phenylpropane
c. propylbenzene
d. propylcyclohexane
What is the name of the molecule on the right?
a. ethylcyclopentane
b. pentylcyclopropane
c. propylcylclopentane
d. propylcyclohexane
What is the name of the molecule on the right?
a. 2-ethylcyclopentene
b. 3-ethylcyclopentene
c. 2-ethyl-2-cyclopentene
d. 5-ethyl-2-cyclopentene
What is the name of the molecule on the right?
a. 2-methylcyclohexene
b. 3-methylcyclohexene
c. 4-methylcyclohexene
d. 5-methylcyclohexene
Select the proper order of stability from least to most stable for the following cycloalkenes:
[pic]
a. A, B, C c. C, A, B
b. B, C, A d. C, B, A
Simple Aromatics - nomenclature
What is the name of the molecule on the right?
a. 2-butylbenzene
b. butylbenzene
c. phenylbutane
d. propylbenzene
What is the name of the molecule on the right?
a. butylbenzene
b. 2-pentylbenzene
c. pentylbenzene
d. phenylpentane
What is the IUPAC name of the compound on the right?
a. pentylcyclohexane
b. cyclopentylhexane
c. pentylbenzene
d. hexylbenzene
What is the IUPAC name of the compound on the right?
a. butylbenzene
b. phenylbutane
c. propylbenzene
d. phenylpropane
Phenyl Branches - nomenclature
What is the IUPAC name of the molecule on the right?
a. 1,1,4-trimethyl-4-phenylbutane
b. 2,4-dimethyl-5-phenylpentane
c. 2,4-dimethyl-2-pentylbenzene
d. 2,4-dimethyl-1-phenylpentane
What is the IUPAC name of the molecule on the right?
a. 2-methyl-3-ethyl-1-phenylbutane
b. 2,3-dimethyl-1-phenylpentane
c. 2,3-dimethyl-1-pentylbenzene
d. 3,4-dimethyl-5-phenylpentane
What is the IUPAC name for the molecule on the right?
a. 2-pentylbenzene
b. 2-phenypentane
c. 1 -methyl-1-phenylbutane
d. pentylbenzene
How many phenyl groups does the following molecule have?
a. 0
c. 2
b. 1
d. 6
Disubstituted benzenes
What is another acceptable name for 1,3-dimethylbenzene?
a. m-dimethylbenzene c. o-dimethylbenzene
b. n-dimethylbenzene d. p-dimethylbenzene
What is another acceptable name for 1,4-dimethylbenzene?
a. m-dimethylbenzene c. o-dimethylbenzene
b. n-dimethylbenzene d. p-dimethylbenzene
What is another acceptable name for 1,2-dimethylbenzene?
a. m-dimethylbenzene c. o-dimethylbenzene
b. n-dimethylbenzene d. p-dimethylbenzene
What is the name of the molecule on the right?
a. ethylmethylbenzene
b. o-ethylmethylbenzene
c. m-ethylmethylbenzene
d. p-ethylmethylbenzene
What is the name of the compound on the right?
e. diethylbenzene
f. m-diethylbenzene
g. o-diethylbenzene
h. p-diethylbenzene
What is the name of the molecule on the right?
a. ethylpropylbenzene
b. o-ethylpropylbenzene
c. m-ethylpropylbenzene
d. p-ethylpropylbenzene
What is the IUPAC name for the isomeric compound on the right?
a. 1,2-dichlorobenzene
b. 1,3-dichlorobenzene
c. 2,2-dichlorobenzene
d. 2,6-dichlorobenzene
Which of the following molecules is p-ethylmethylbenzene?
a. [pic] b. [pic]
c. [pic] d. [pic]
Units of Unsaturation/general formulas
What type of hydrocarbon is the compound on the right? CH3-CH2-CH2-CH2-CH2-CH3
a. aliphatic c. cyclic
b. aromatic d. unsaturated
Which hydrocarbon is saturated?
a. C6H6 c. C6H12
b. C6H10 d. C6H14
Which is the formula of a saturated hydrocarbon?
a. C2H2 c. C2H4
b. C5H8 d. C5H12
Which is the formula of a saturated hydrocarbon?
a. CH2CH2 c. C6H6
b. CH3CHCH2 d. (CH3)3CH
A saturated continuous-chain hydrocarbon with seven carbons is _____.
a. cycloheptene c. heptene
b. heptane d. heptyne
Which of the following compounds is an unsaturated hydrocarbon?
a. methane c. nonane
b. propyne d. ethyl
How many units of unsaturation does the molecular formula C5H8 have?
a. none c. two
b. one d. three
How many units of unsaturation does the molecular formula C7H12 have?
a. none c. two
b. one d. three
Which could be a molecular formula for an organic chemical with one ring and one double bond?
a. C5H10 c. C5H8
b. C6H14 d. C6H12
Which could be a molecular formula for an organic chemical with one ring?
a. C5H10 c. C5H8
b. C6H14 d. C6H10
Which could be a molecular formula for a non-cyclic hydrocarbon with two double bonds?
a. C5H10 c. C5H8
b. C6H14 d. C6H12
What is the molecular formula for 3,3-diethyl-4-methyl-1-hexyne?
a. C10H18 c. C11H22
b. C11H20 d. C12H22
Which formula represents a member of the alkene series?
a. C3H6 c. C2H2
b. C2H6 d. C6H6
Which formula represents a member of the alkane family?
a. C3H6 c. C2H2
b. C2H6 d. C6H6
What is the general formula for a continuous-chain alkane?
a. CnHn c. CnH2n-2
b. CnHn+2 d. CnH2n+2
To which class of aliphatic hydrocarbons does C25H52 belong?
a. alkanes c. alkynes
b. alkenes d. aromatics
Which of the following molecules is a saturated hydrocarbon?
a. [pic] b. [pic]
c. [pic] d. [pic]
Isomers:
Which molecule is NOT an isomer of C4H8?
a. [pic] c. [pic]
b. [pic] d. [pic]
Which molecule is NOT an isomer of C5H12?
a. [pic] c. [pic]
b. [pic] d. [pic]
C8H16 could have isomers with
a. one ring or one double bond c. one ring and one double bond
b. one triple bond d two rings
Which structural formula represents an isomer of 2-pentyne?
a. c.
b. [pic] d. [pic]
Which compound is an isomer of methylpropane?
a. butane c. pentane
b. cyclopropane d. propane
Which of the following compounds is a structural isomer of butane?
a. 2-methylbutane c. 2,2-dimethylbutane
b. 2-methylpropane d. 2,2-diethylpropane
Which pairs of molecules are structural isomers?
a. cyclohexane and 2,2-dimethylbutane
b. cyclohexene and 3,3-dimethyl-1-butyne
c. methylcyclobutane and 2-pentyne
d. 2-methylpentyne and 2-methylpentene
A structural isomer of hexane is _____.
a. benzene c. cyclohexane
b. 2,2-dimethylbutane d. 2-methylpentene
Which compound can have isomers?
a. C2H4 c. C2H2
b. C2H6 d. C4H8
How many structural isomers exist for the alkene CH2Br2?
a. 1 c. 3
b. b. 2 d. 4
Which compound is an isomer of CH3.CH2.CH2.CH2.OH
a. CH3CH2OCH3 c. CH3CH2CH2CH3
b. CH3CH2CH2OH d. CH3CH(OH)CH2CH3
Which of the following pairs of compounds are isomers?
a. diethyl ether and 1-butanol b. 2-pentanone and 2-pentanol
c. pentanal and methyl butanoate d. propanoic acid and propanal
Structural isomers have _____.
a. the same molecular formula
b. different physical and chemical properties
c. the same elemental composition
d. all of the above
Which of the following pairs of compounds are isomers?
a. propanal and 1-propanol
b. propanoic acid and propyl propanoate
c. propanone and propanal
d. propyl ether and 1-propanol
Isomer - Short Answer
1a) A student is told to draw the structural diagram of the compound with formula C4H10 . Confused, the student tells the naive chemistry-challenged person that the task is impossible.
a) Why can=t the student show the structure of C4H10? (2)
b) Rephrase the question by changing one word so that the question can be answered, and then answer it. (Keep the flavor of the question - don't change it completely!) (4)
1a) Give a brief explanation, using two examples, as to why the numbers are necessary for identifying an organic compound sometimes, but not other times. (4)
b) Identify which of the following names need numbers in front to identify them completely: butanol, propanal, pentanone, hexene, butanoic acid, methylpentane.(3)
How many different answers should you get to the question, "What is the boiling point of C3H8O?" Explain with the use of structural diagrams, names and a brief discussion of intermolecular attractions.
Draw structural formulas for and name four isomers of C4H7Cl.
Halocarbons
Which substituent would allow a compound to be classified as an alkyl halide?
a. fluorine c. oxygen
b. nitrogen d. sulfur
The IUPAC name for the compound (CH3)2C(CH2.CH3).CH2.CHCl.CH3 is:
a. 5-chloro-3,3-dimethylhexane c. 2-chloro-4-methyl-4-ethylpentane
b. 4-chloro-2-ethyl-2-methylpentane d. 1-chloro-1,3,3,3-trimethylpentane
What is the name of the molecule on the right?
a. 2-dichloro-3-methylpentane
b. 2,2-dichloro-3-methylpentane
c. 4,4-dichloro-3-methylpentane
d. 4,4-dichloro-3,5-dimethylbutane
What is the name of the molecule on the right?
a. 2,3-dichloro-2-methylpentane
b. 1,2-dichloro-1,1-dimethylbutane
c. 2,3-chloro-2-methylpentane
d. 3,4-dichloro-4-methylpentane
The correct name for the molecule on the right is:
a. 1,4,4-trifluoro-2-bromopentane
b. 2-bromo-1,4,4-trifluoropentane
c. 2,2,5-trifluoro-4-bromopentane
d. 4-bromo-2,2,5-trifluoropentane
Alcohols
What is the name of the molecule on the right?
a. butanone
b. 2-butanol
c. 2-butanal
d. butyl ether
What is the name of the molecule on the right?
a. 3-pentanone
b. 3-pentanal
c. 3-pentanol
d. pentanoic acid
What is the correct IUPAC name for the compound shown below?
CH3.CH2.CH(CH2.CH3).CH(OH).CH3
a. 3-ethyl-4-pentanol
b. 2-methyl-5-hexanol
c. 3-ethyl-2-pentanol
d. 3-ethyl-2-heptanol
The correct IUPAC name for the compound CH3.CH2.CH2.C(CH3)2.OH is
a. 1-hexanol c. 1- dimethylbutanol
b. 1,1-dimethyl-1-butanol d. 2-methyl-2-pentanol
Ethers
Which molecule is an ether?
a. [pic] c. [pic]
b. [pic] d. [pic]
Which of the following is an ether?
a. [pic] c. [pic]
b. [pic] d. [pic]
What is the name of the molecule on the right?
a. butanal
b. methylpropyl ether
c. butanone
d. methyl propanoate
What is the name of the molecule on the right?
a. pentanal
b. ethylpropyl ether
c. pentanone
d. ethyl propanoate
Aldehydes
Which molecule is an aldehyde?
a. [pic] c. [pic]
b. [pic] d. [pic]
Which of the following is an aldehyde?
a. [pic] c. [pic]
b. [pic] d. [pic]
What is the IUPAC name of the molecule on the right?
a. butanal
b. 1-butanone
c. butanoic acid
d. propanal
What is the IUPAC name of the molecule on the right?
a. butanal
b. 1-butanone
c. butanoic acid
d. propanal
Which of the following is an aldehyde?
a. butanone c. ethane
b. ethanol d. pentanal
Which of the following is an aldehyde?
a. butanal b. ethanone
c. ethanol d. pentanoic acid
Ketones
What is the IUPAC name of the molecule on the right?
a. ethylpropyl ether
b. 3-hexanal
c. 3-hexanone
d. methyl butanoate
What is the IUPAC name of the molecule on the right?
a. diethyl ether
b. 2-pentanone
c. 3-pentanone
d. 3-pentanal
Which of the following is a ketone?
a. [pic] c. [pic]
b. [pic] d. [pic]
Which condensed structural formula represents a ketone?
a. CH3CH2CH2OH c. CH3COCH3
b. CH3CH2CHO d. CH3CH2COOH
Carboxylic Acids
What is the IUPAC name of the molecule on the right?
a. butanone
b. ethanoic acid
c. methy propanoate
d. propanoic acid
What is the IUPAC name of the molecule on the right?
a. butanal
b. butanoic acid
c. methy propanoate
d. propanoic acid
What is the IUPAC name of the molecule on the right?
a. pentanal
b. pentanoic acid
c. methy butanoate
d. pentanone
Esters
What is the IUPAC name of the molecule on the right?
a. butyl ethanoate
b. ethyl propanoate
c. ethyl butanoate
d. propyl ethanoate
What is the IUPAC name of the molecule on the right?
a. ethyl methanoate
b. methyl ethanoate
c. ethanoic acid
d. propanoic acid
What is the IUPAC name of the molecule on the right?
a. ethyl propanoate
b. methyl butanoate
c. butyl methanoate
d. methyl propanoate
Trivial Names
What is the IUPAC name of the molecule on the right?
a. acetylene
b. formaldehyde
c. phenol
d. toluene
What is the IUPAC name of the molecule on the right?
a. acetylene
b. formaldehyde
c. phenol
d. toluene
Fractional Distillation/Sources of hydrocarbons
Which molecule would condense closer to the top of a fractional distillation tower?
a. C5H12 c. C14H30
b. C10H22 d. C20H42
Which molecule would condense closer to the bottom of a fractional distillation tower?
a. C5H12 c. C14H30
b. C10H22 d. C20H42
Which is the correct statement regarding fractional distillation?
a. The mixture of hydrocarbons in crude oil are converted into the various fractions (gasoline, furnace oil, etc.) by chemical reactions
b. Substances with high boiling points will condense lower in the fractional distillation tower.
c. Fractions with very low boiling points will condense before the fractions with high boiling points
d. Crude oil from different sources, when distilled in a fractionating tower, will yield the same percent of gasoline
Which compound in crude oil will be the first to evaporate relative to the other hydrocarbons listed?
a. decane c. heptane
b. nonane d. octane
What is not a source of raw materials for petrochemical industries?
a. coal deposits c. crude oil
b. mineral deposits d. natural gas
What is the main hydrocarbon component of natural gas?
a. benzene c. ethane
b. methane d. propane
Which type of coal has the highest carbon content?
a. anthracite c. lignite
b. bituminous d. peat
Which process involves the conversion of once living organic matter to fossil fuels?
a. carbonization c. combustion
b. nuclear fusion d.. photosynthesis
Shapes of molecules
The bonding shape around every carbon in propane is
a. bent c. tetrahedral
b. linear d. trigonal planar
What is the shape of a methane molecule?
a. bent c. pyramidal
b. linear d. tetrahedral
The bonding shape around both carbons in ethyne is
a. bent linear tetrahedral trigonal planar
Which of the following molecules is completely flat or planar?
a. a. ethene b. ethane c. propene d. cyclohexane
Which description best describes the boding shape around the carbons in the molecule on the right?
a. trigonal planar
b. linear
c. tetrahedral
d. cyclic
Short Answer:
1. (a) Draw Lewis diagrams for ethane and ethyne.
(b) Describe the shape around the carbon atoms in ethane versus ethyne.
(c) How does the shape and arrangement of bonding electrons influence the reactivity of ethane versus ethyne?
Solubility
Which substance would be most soluble in water?
a. propanoic acid c. propanal
b. propanone d. propane
Which substance would be least soluble in water?
a. propanoic acid c. propanal
b. propanone d. propane
Which substance is immiscible with water?
a. 2-butanol c. ethanal
b. 2-methyl-3-heptene d. methanoic acid
In which of the following solvents would candle wax, C25H52, dissolve in the best?
a. H2O c. C9H18
b. CH3OH d. C3H7OH
In which of the following compounds is hexane most likely to dissolve?
a. acetic acid c. ethyl alcohol
b. decane d. water
nonane
Boiling Points
Which substance would have the highest boiling point?
a. C7H12 c. C14H28
b. C9H16 d. C22H40
Which of the following compounds has the lowest boiling point?
a. heptane c. 2,3-dimethylpentane
b. 2-methylhexane d. 2,2,3-trimethylbutane
Which substance would have the lowest boiling point?
a. C7H12 c. C14H28
b. C9H16 d. C22H40
Which alkene has the highest boiling point at atmospheric pressure?
a. C2H4 c. C4H8
b. C3H6 d. C5H10
What is the main force that influences boiling points in pure hydrocarbons?
a. covalent bonding c. hydrogen bonding
b. dipole-dipole attractions d. London Dispersion Forces
Which property is generally accepted as an indicator of the strength of intermolecular forces within a substance?
a. boiling point c. isomerism
b. London dispersion force d. solubility
Alkanes, alkenes, and alkynes with the same number of carbons have:
a. similar boiling and melting points primarily because they have nearly the same molecular weight
b. similar boiling and melting points primarily because they have similar polarities
c. similar boiling and melting points primarily because they are nearly equal in stability
d. vastly different boiling and melting points
If alkenes of four carbons or less exist as gases at room temperature, how many alkenes exist as gases under these conditions?
a. 2 c. 4
b. 3 d. 5
What is the physical state of the smallest alkanes (C1-C4) at room temperature?
a. gas c. solid
b. liquid d. gas or liquid
Intermolecular Forces
In which substance would London dispersion forces be the only intermolecular force of attraction?
a. 1-pentanol c. pentanal
b. pentanoic acid d. pentyne
Which substance would be able to form hydrogen bonds to water but would not have any hydrogen bonding between their own molecules?
a. ethanol c. propanal
b. propanoic acid d. propanol
Hydrogen bonding is most noticeable in
a. alkanes c. esters
b. alkynes d. organic acids
Why is a carbon-hydrogen bond essentially nonpolar?
a. Neither atom is ionic.
b. Free electrons cancel any polarity.
c. The electron pair is shared almost equally.
d. Van der Waals forces overcome polarity.
Lewis Dot Diagrams/Carbon Bonding
How many valence electrons surround a carbon atom?
a. 1 c. 3
b. 2 d. 4
How many covalent bonds does each carbon atom participate in an organic compound?
a. 1 c. 3
b. 2 d. 4
Which is the correct Lewis Dot diagram for acetylene, C2H2?
a. [pic] c. [pic]
c. [pic] d. [pic]
Benzene Bonding
What compound is the simplest of the arenes?
a. benzene c. ethyne
b. ethene d. methane
Which of the following molecules does NOT have delocalized electrons?
a. benzene c. cyclohexane
b. 2-phenylpentane d. toluene
The compound benzene puzzled chemists for many years. Empirical research indicates that carbon-carbon bonds in benzene are
a. all carbon-carbon single bonds
b. all carbon-carbon double bonds
c. neither double nor single bonds
d. easily broken in chemical reactions.
Which chemical has delocalized electrons?
a. [pic] b. [pic]
c. [pic] d. [pic]
What distinguishes benzene and benzene compounds from other organic compounds?
a. benzene and benzene compounds are planar molecules
b. carbon atoms in benzene have 120° bond angles
c. carbon atoms in the benzene ring have just three bonding electrons
d. carbon-carbon bonds in benzene involve delocalized bonding electrons
Functional Groups/hydrocarbon derivatives
Which of the following is a hydrocarbon derivative?
a. C3H8 c. C9H18
b. CH4 d. C3H70H
An arrangement of several atoms which gives characteristic properties to an organic molecule is known as a(an)
a. carboxyl group c. group
b. functional group d. alkyl group
What is primarily responsible for the chemical properties of a hydrocarbon derivative like ethanol?
a. its delocalized electrons c. its functional group
b. its level of saturation d. its solubility in water
In the general formula for alcohols, R-OH, the "R' represents
a. radon c. the functional group
b. CH3 only d. an alkyl group
The functional group for aldehydes is:
a. hydroxyl c. carboxyl
b. carbonyl d. ester
The functional group for ketones is:
c. hydroxyl c. carboxyl
d. carbonyl d. ester
The functional group for alcohols is:
e. hydroxyl c. carboxyl
f. carbonyl d. ester
The functional group for carboxylic acids is:
g. hydroxyl c. carboxyl
h. carbonyl d. ester
Which compound contains the functional group called hydroxyl?
a. CH3OH c. HCOOH
b. H2CO d. NH4CH3COO
The functional group for alcohols is
a. hydroxyl c. carboxyl
b. carbonyl d. ester
Organic Reactions
Complete the following reactions by identifying reaction type, predicting products where necessary, drawing structures for ALL organic reactants and products and naming ALL products. Indicate if more than two products are possible.
Respiration/Photosynthesis:
Which biological process produces glucose from carbon dioxide and water?
a. carbonization c. fusion
b. photosynthesis d. respiration
Cracking/Reforming
Which reaction type uses ethene and low molecular weight hydrocarbons and converts them into gasoline grade hydrocarbons?
a. cracking c. esterification
b. elimination d. reforming
What is the name of the process in which large molecules are broken down into smaller molecules in order to increase the yield of gasoline from petroleum?
a. polymerization c. esterification
b. hydrogenation d. cracking
Which chemical reaction may be used to convert straight-chain aliphatic hydrocarbons to alkylated or branched hydrocarbons?
a. elimination c. esterification
b. reforming d. substitution
n-decane + H2 ( butane + _______
Substitution
Which is NOT a possible product in the reaction between benzene and 2 mol of bromine?
a. 1,3-dibromobenzene c. 1,2,3,4-tetrabromobenzene
b. o-dibromobenzene d. hydrogen bromide
Which is NOT a possible product in the reaction between benzene and 2 mol of chlorine?
a. 1,2-dichlorobenzene c. 1,2,4,5-tetrachlorobenzene
b. p-dichlorobenzene d. hydrogen chloride
Which pairs of reactants are most likely to react by a substitution reaction?
I. H2 II. Cl2 III. C2H4 IV. C2H6
a. I and III c. I and IV
b. II and III d. II and IV
Which pairs of reactants are most likely to react by a substitution reaction?
I. Br2 II. HBr III. C2H6 IV. C2H4
a. I and III c. I and IV
b. II and III d. II and IV
Which type of compound will undergo a substitution reaction with a halogen?
a. an alkane c. an alkyne
b. an alkene d. a ketone
Based on the generalizations for reaction types, butane and fluorine gases react by
a. addition c. combustion
b. esterification d. substitution
Short answer:
propane + 1 mol chlorine
pentane + 1 mol bromine
benzene + 2 mol bromine
m-dimethylbenzene + chlorine
butane + 2 mol bromine
pentane + Br2
hexane + chlorine [pic]
Addition
Which IS a product of the reaction between 2-butene and 1 mol of chlorine?
a. 1,2-dichlorobutane c. 1,3-dichlorobutane
b. 2,3-dichlorobutane d. 1-4-dichlorobutane
Which IS a product of the reaction between propene and 1 mol of chlorine?
a. 1,2-dichloropropane c. hydrogen
b. 1,3-dichloropropane d. 1-chloropropane
Which is NOT a product of the reaction between 1-pentyne and 2 mol of hydrogen bromide?
a. 1,1-dichloropentane c. 1,3-dichloropentane
b. 1,2-dichloropentane d. 2,2-dichloropentane
What type of reaction is C2H4+ H2 ( C2H6 ?
a. addition c. condensation
b. substitution d. esterification
Which equation represents an addition reaction?
a. CH3CH3 + Cl2 ( CH3CH2Cl + HCl
b. CH2CH2 + Cl2 ( CH2ClCH2Cl
c. CH3CH2Cl + OHB ( CH2CH2 + H2O + ClB
d. CH2CH2 + CH3CH3 ( (CH3)2CHCH3
How many products will result when 1-butene reacts with water?
a. 1 c. 3
b. 2 d. 4
How many products will result when 2-butene reacts with water?
a. 1 c. 3
b. 2 d. 4
Which organic reactant will produce 3-chloropentane when reacted with hydrogen chloride?
a. pentane c. 2-pentene
b. 1-pentene d. 2-pentyne
Short answer
2-pentyne + excess HCl
2-pentyne + 2 mol HCl
2-butyne + 2 mol HBr
1-butyne + 2 mol HCl
3-octene + hydrogen iodide
1-pentene + water
1-butene + water
3-heptene + water
4-methyl-1-butyne + 1 mol hydrogen
Esterfication
Which of the following pairs of compounds could be combined to synthesize the compound responsible for the odor of pears, pentyl ethanoate?
a. 1-pentanol and ethanol c. 1-pentanol and ethanoic acid
b. ethanal and pentanoic acid d. ethanol and 1-pentene
Which substance would be the best choice as a catalyst for a reaction between octanoic acid and ethanol?
a. acetic acid c. methanol
b. sodium hydroxide d. sulfuric acid
What is the organic product of the reaction of methanol and ethanoic acid?
a. propanone c. ethyl methanoate
b. propanal d. methyl ethanoate
Short answer
ethanoic acid + 1-pentanol
propanol + butanoic acid
methanoic acid + 1-pentanol
1-butanol + _________________ ( butyl propanoate
Hydrocarbon Combustion
When hydrocarbons are burned completely, which product is always formed?
a. amorphous graphite c. limewater
b. carbon dioxide d. methane
Short answer
2-methyl-1-butene + oxygen (Balance this reaction)
2-methyl-1-hexene + oxygen (Balance this reaction)
3-methyl-1-pentyne + oxygen
3,4-diethyl-2-pentene + oxygen
Elimination
Which substance will undergo an elimination reaction when reacting with hydroxide ions?
a. 2-fluoropropane c. ethanoic acid
b. methyl methanoate d. propanal
Which compound, when heated in the presence of a strong acid, will produce a second compound that will react quickly with bromine, even in the dark?
a. acetylene c. 1-hexanol
b. 2-butene d. pentane
Which reaction will not produce an alkene?
a. 2-chlorohexane is heated with sodium hydroxide
b. 2-pentyne and hydrogen are mixed in the presence of a platinum catalyst
c. 1-propanol is warmed with butanoic acid in the presence of a strong acid
d. 3-propanol is warmed in the presence of a strong acid
Short answer
2-chlorobutane + hydroxide ions
2-chlorobutane + sodium hydroxide
2-pentanol is warmed in the presence of a strong acid
ethanol [pic]
3-heptanol [pic]
Reaction type: _______________________
Identifying Polymerization
Identify the reaction type:
[pic]
a. addition polymerization c. condesation polymerization
b. esterification d. hydrocarbon combustion
Identify the reaction type:
[pic]
a. addition polymerization c. condesation polymerization
b. esterification d. hydrocarbon combustion
What monomer was used to produce the polymer:
[pic]
a. [pic] b. [pic]
c. [pic] d. [pic]
Condensation Polymerization
Which polymer was produced by condensation polymerization?
a. [pic]
b. [pic]
c. [pic] d. [pic]
Long answer:
Proteins are the building blocks of the human body. They are composed of chains of amino acids, and make up our skin, nails, hair and connective tissue. The type of protein formed depends upon the sequence of the amino acids in the chain.
Some amino acids are given below.
alanine [pic]glycine [pic]
cysteine [pic] Threonine [pic]
a. What type of reaction will link these amino acids into a long chained protein?
b. What are the chemical characteristics of these molecules that allow them to form long chains? Pick one of the amino acids to illustrate your answer.
c. The protein in hair will curl around in a helix shape, held together by hydrogen bonds. Draw a dotted line to show where hydrogen bonding could occur if cysteine and threonine were close together on two different protein chains. (2)
Addition Polymerization
Which substance will undergo addition polymerization?
a. 1-propanol c. propanal
b. propanone d. propene
Which monomer will produce the polymer on the right?
a. 1-pentene
b. 2-pentene
c. ethylmethylethane
d. pentane
Which synthetic polymer is the product of addition polymerization?
a. cellulose c. ribonucleic acid (RNA)
b. protein d. teflon
Short answer
addition polymerization reaction with 1-pentene
addition polymerization reaction with 1-butene
n 2-pentyne
Long Answer Questions:
When ethene reacts with chlorine in the absence of light, only one product forms. However, if ethene reacts with chlorine in the presence of light, over a long period of time, many products are formed.
a. Identify the reaction type when ethene reacts in the absence of light, and write equation to show the product formed. Name and draw the product. (4%)
b. Identify the two reaction types when ethene reacts in the presence of light, and write an equation to illustrate each. Name and draw all possible products. (8%)
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