Chemistry ch. 13

Much more

Secondary (2°) carbocations are more or less stable than primary (1°) carbocations?

high-density polyethylene.

The molecules in straight-chain polyethylene pack closely together, giving a rigid material called ____ ____ _______

D

Which choice represents the carbon skeleton of 1,6-octadiene? Question 41 options: A) C-C=C-C-C=C-C-C B) C=C=C-C-C-C-C-C C) C=C-C-C=C-C=C-C D) C-C=C-C-C-C-C=C E) C-C=C-C=C-C-C-C

Polycyclic

_______ aromatic compounds are substances that have two or more benzene-like rings joined together by a common bond.

Markovnikov's rule

—In the addition of HX to an alkene, the major product arises from the H attaching to the double-bond carbon that has the larger number of H atoms directly attached to it, and the X attaching to the carbon that has the smaller number of H atoms attached.

alcohol

An alkene will not react with pure water alone. If a small amount of strong acid catalyst is added, an addition reaction takes place to yield an ______

low-density polyethylene

Branched polyethylene cannot pack together as tightly and instead forms a flexible material called ___ _____ _______

Alkenes and Alkynes

Nonpolar; insoluble in water; soluble in nonpolar organic solvents • Less dense than water • Flammable; nontoxic • display cis-trans isomerism when each double-bond carbon atom has different substituents. • Chemically reactive at the multiple bond

polyethylene.

When polymerized ethylene yields ______

C

Which molecule can have cis-trans isomers? Question 17 options: A) CH3CH=CCl2 B) (CH3)2C=C(CH3)2 C) CH3CH=CHCl D) (CH3)2C=CHCH3 E) CH3CH=C(CH3)2

Nitration

_____ is the substitution of a nitro group NO2 for a hydrogen on an aromatic ring.

Aromatic

_______—The class of compounds containing benzene-like rings

Pentene

5 Carbon chain containing a double bond

Hexene

6 Carbon chain containing a double bond

Hexyne

6 Carbon chain containing a triple bond

Rearrangement

A _______ reaction is a general reaction type in which a molecule undergoes bond reorganization to yield an isomer.

Substition

A ________ reaction is a general reaction type in which an atom or group of atoms in a molecule is replaced by another atom or group of atoms.

phenyl

A benzene ring itself may be considered a substituent group attached to another parent compound. • When this happens, the name ____ is used

reaction mechanism

A description of the individual steps by which old bonds are broken and new bonds are formed in a reaction is called a _____ ______

initiator to an alkene

A reaction mechanism begins by addition of an _______ to an ______; this results in the breaking of one of the bonds making up the double bond.

E

A rearrangement reaction can best be described as a reaction in which Question 67 options: A) a single reactant splits into two products. B) two reactants combine to form one new product with no extra atoms. C) a hydrocarbon reacts with oxygen to produce CO2, H2O, and energy. D) two reactants exchange atoms to give two new products. E) a single reactant undergoes reorganization of its chemical bonds, producing an isomer of the reactant.

D

A substitution reaction can best be described as a reaction in which Question 26 options: A) two reactants combine to form one new product with no extra atoms. B) a hydrocarbon reacts with oxygen to produce CO2, H2O, and energy. C) a single reactant undergoes reorganization of its chemical bonds, producing an isomer of the reactant. D) two reactants exchange atoms to give two new products. E) a single reactant splits into two products.

B

According to Markovnikov's rule, when HCl reacts with the molecule shown, which product will result? (CH3)2C=CHCH3 + HCl → ????? Question 46 options: A) (CH3)2CClCHClCH3 B) (CH3)2CClCH2CH3 C) (CH3)2CHCH2CH2Cl D) (CH3)2CHCHClCH3 E) Cl2CHCHClCH3

Hydration

Addition of Water to Alkenes: ______

A

Alkanes and alkenes are similar in all of the following properties except Question 54 options: A) reactivity. B) flammability. C) insolubility in water. D) lack of toxicity. E) solubility in non-polar solvents.

E

Alkenes and simple aromatics are similar in all of the following properties except Question 66 options: A) flammability. B) insolubility in water. C) nonpolarity. D) solubility in non-polar solvents. E) lack of toxicity.

hydrohalogenation

Alkenes react with hydrogen bromide (HBr) to yield alkyl bromides and with hydrogen chloride (HCl) to yield alkyl chlorides in ________ reactions.

E

All of the following are common reactions of benzene except Question 50 options: A) sulfonation. B) bromination. C) nitration. D) chlorination. E) hydrogenation.

D

All of the following are examples of addition reactions of alkenes except Question 44 options: A) bromination. B) hydrogenation. C) chlorination. D) oxidation. E) hydration.

D

All of the following are general properties of alkenes except Question 34 options: A) flammable. B) may exist as cis-trans isomers. C) low boiling points. D) less reactive than the corresponding alkanes. E) soluble in non-polar (organic) solvents.

Elimination

An _______ reaction is a general reaction type in which a saturated reactant yields an unsaturated product by losing groups from two adjacent atoms.

D

An addition reaction can best be described as a reaction in which Question 38 options: A) a hydrogen reacts with oxygen to produce CO2, H2O, and energy. B) a single reactant undergoes reorganization of its chemical bonds, producing an isomer of the reactant. C) a single reactant splits into two products. D) two reactants combine to form one new product with no extra atoms. E) two reactants exchange atoms to give two new products.

E

An elimination reaction can best be described as a reaction in which Question 42 options: A) two reactants exchange atoms to give two new products. B) a hydrocarbon reacts with oxygen to produce CO2, H2O, and energy. C) two reactants combine to form one new product with no extra atoms. D) a single reactant undergoes reorganization of its chemical bonds, producing an isomer of the reactant. E) a single reactant splits into two products.

D

Another name for o-nitrotoluene is Question 24 options: A) 4-nitrotoluene. B) 1-nitrotoluene. C) 3-nitrotoluene. D) 2-nitrotoluene.

electrophilic aromatic substitution reaction.

Aromatic compounds usually undergo a special type of substitution reaction known as an ________ ________ _________ ________

ends and sides

As a consequence of their rigid nature, alkenes possess _____ and _____

C6H6

Benzene is a flat, symmetrical molecule with the molecular formula _____ .

unsaturation

Bromine (Br2 ) can be used as a test for multiple bonds and _______ of fats:

B

Chemical reactions involving double bonds are generally referred to as ________ reactions. Question 19 options: A) oxidation B) addition C) substitution D) combustion E) reduction

B

Cis-trans isomerism occurs when A) a branched alkane has a halogen added to two adjacent carbon atoms. B) the carbons in an alkene double bond each have two different substituent groups. C) hydrogen is added to both of the carbon atoms in a double bond. D) an alkene is hydrated according to Markovnikov's Rule. E) the carbons in the para position of an aromatic have the same substituent groups.

ortho, meta, and para

Disubstituted benzenes are unique in that the relational descriptors _____, ______, and _____ may be used in place of 1,2-, 1,3-, and 1,4-.

C

Ethylene and acetylene are the common names for the molecules ________ and ________, respectively Question 13 options: A) C2H4 and C2H6 B) C2H2 and C2H6 C) C2H4 and C2H2 D) C2H4 and C3H6 E) C2H6 and C3H8

identical

Experimental evidence shows that all six carbon-carbon bonds in benzene are _______

D

How many hydrogen atoms are contained in a molecule of 1,4-hexadiene? Question 63 options: A) 14 B) 18 C) 12 D) 10 E) 6

D

How many hydrogen atoms are contained in a molecule of cyclopentene? Question 58 options: A) 6 B) 12 C) 10 D) 8 E) 5

B

In organic chemistry, the term unsaturated means a molecule Question 43 options: A) that is formed from many smaller molecules. B) that contains one or more multiple bonds between carbon atoms. C) with a specific six-membered ring structure. D) that has the maximum number of carbon-hydrogen bonds possible. E) that can react by taking up one or more water molecules.

A

In the addition of HX to a double bond, the hydrogen goes to the carbon that already has more hydrogens. This is a statement of Question 25 options: A) Markovnikov's rule. B) LeChatelier's principle. C) the double bond rule. D) Zatseff's rule. E) the rule of "less is better".

toluene, phenol, and aniline.

Many substituted aromatic compounds have common names in addition to their systematic names. - Methylbenzene is ________ - Hydroxybenzene is ______ - Aminobenzene is ______

B

Markovnikov's Rule refers to the Question 33 options: A) color of a molecule containing multiple double bonds. B) orientation an unsymmetrical reagent will take when added to an unsymmetrical alkene. C) ideal bond angle between substituents on a double bond. D) temperature difference observed in the boiling points of cis and trans alkenes. E) rate of hydrogen addition to an alkene with alkyl group substituents.

addition

Most of the reactions of carbon-carbon multiple bonds are ______ reactions.

C

On the basis of the number of carbon-hydrogen bonds, all of the following families of compounds can be considered unsaturated except Question 4 options: A) alkynes. B) alkenes. C) alkanes. D) arenes. E) none of the above

cross-linking agent

Polymer rigidity is controlled by addition of a ____ ______ _____, typically 1-2% of a dialkene (an alkene containing two double bonds), whose role is to covalently link two chains of monomer units together

unstable

Primary (1°) carbocations are so _____ that they almost never form.

hydrocarbons

Simple aromatic _______ are nonpolar, insoluble in water, volatile, and flammable.

More

Tertiary (3°) carbocations are more or less stable than secondary (2°) carbocations?

C

The addition of HF to 2-butene produces Question 35 options: A) 1,2-difluorobutane. B) 1-fluorobutane. C) 2-fluorobutane. D) 2,3-difluorobutane. E) The reaction doesn't occur

B

The bond angle about a carbon atom involved in a double bond is Question 59 options: A) 109.5°. B) 120°. C) 180°. D) 90°. E) 105°.

C

The bond angle about a carbon atom involved in a triple bond is Question 69 options: A) 90°. B) 109.5°. C) 180°. D) 120°. E) 105°.

A

The cause of cis-trans isomerism is Question 21 options: A) lack of rotation of the double bond. B) short length of the double bond. C) vibration of the double bond. D) stability of the double bond. E) strength of the double bond.

C

The commonly accepted mechanism for explaining alkene reactions involves formation of Question 68 options: A) carbanions. B) carbon atoms with four electrons. C) carbocations. D) carbon atoms which have lost all their electrons. E) carbon atoms with 10 electrons.

A

The concept that explains the properties of aromatic compounds based on a structure that is an average among two possible structures is Question 8 options: A) resonance. B) cis-trans isomerism. C) polymerization. D) double bonding. E) oxidation.

B

The monomer unit used to produce polypropylene is Question 9 options: A) CH2=CHCH2Cl. B) CH2=CHCH3. C) CHCl=CH2. D) CH2=CH2. E) CH3CH2CH2CH3.

C

The monomer used to make the polymer polyvinyl chloride is: Question 39 options: A) CH2=CHCN B) CH2=CF2 C) CH2=CHCl D) CH2=CH-C6H5 E) CF2=CF2

E

The most common reactions involving aromatics are ________ reactions. Question 64 options: A) addition B) reduction C) elimination D) oxidation E) substitution

A

The name of the molecule shown is Question 52 options: A) 3-chloro-2-methyl-1-butene. B) cis-3-chloro-2-methyl-2-butene. C) 3-chloro-2-methylene-butane. D) trans-3-chloro-2-methyl-2-butene. E) 2-chloro-3-methylene-butane.

B

The name of the polymer formed from CH2=CH2 is Question 22 options: A) polyvinyl chloride. B) polyethylene. C) polypropylene. D) polystyrene. E) none of the above

A

The organic chemical produced in the largest quantities in the U.S. is Question 11 options: A) ethylene B) benzene. C) polyethylene. D) octane. E) sulfuric acid.

E

The process used to produce simple alkenes is Question 20 options: A) condensation of small molecules. B) smelting of ores. C) polymerization of monomers. D) distillation of crude oil. E) cracking of alkanes.

A

The starting material for polymerization reactions is a(an) Question 16 options: A) monomer. B) catalyst. C) isomer. D) dimer. E) alkane.

D

The term used to describe the geometry of a carbon atom involved in a double bond is Question 5 options: A) distorted tetrahedral. B) tetrahedral. C) linear. D) trigonal planar. E) perpendicular.

A

The term used to describe the geometry of a carbon atom involved in a triple bond is Question 3 options: A) linear. B) trigonal planar. C) perpendicular. D) tetrahedral. E) distorted tetrahedral.

C

What is the IUPAC name of the molecule shown? CH2=CH—CH=CH2 Question 2 options: A) diethylene B) 1,1-butadiene C) 1,3-butadiene D) 1,4-butadiene E) 1,2-butadiene

A

What is the ideal angle between the H-C-C bond in acetylene? Question 28 options: A) 180° B) 90° C) 120° D) 109.5° E) none of the above

D

What is the ideal angle between the H-C-C bond in ethylene? Question 49 options: A) 180° B) 90° C) 109.5° D) 120° E) none of the above

D

What is the ideal angle between the H-C-H bond in methane? Question 31 options: A) 90° B) 180° C) 120° D) 109.5° E) none of the above

B

What is the name of the product when 1-pentene reacts with Cl2? Question 6 options: A) 2,2-dichloropentane B) 1,2-dichloropentane C) 2,3-dichloropentane D) 1,1-dichloropentane

D

When 2-butene reacts completely with bromine, the product is A) 3-bromobutane. B) 2-bromobutane. C) 1,3-dibromobutane. D) 2,3-dibromobutane. E) 1,2-dibromobutane.

B

When an alkene undergoes a hydration reaction the product is an Question 47 options: A) aromatic. B) alcohol. C) alkane. D) ether. E) alkyne.

D

When an alkene undergoes hydrogenation, the product is an Question 65 options: A) alcohol. B) alkyne. C) aromatic. D) alkane. E) alkene.

polypropylene.

When polymerized propylene yields _______

polystyrene.

When polymerized styrene yields ________

A

When the aromatic ring is named as a side chain or functional group, it is referred to as the ________ group. Question 37 options: A) phenyl B) toluyl C) xylyl D) benzoyl E) benzyl

B

Which choice represents the carbon skeleton of 2,4-octadiene? Question 45 options: A) C=C=C-C-C-C-C-C B) C-C=C-C=C-C-C-C C) C=C-C-C=C-C=C-C D) C-C=C-C-C=C-C-C E) C-C=C-C-C-C-C=C

D

Which choice represents the carbon skeleton of 2,5-octadiene? Question 7 options: A) C-C=C-C-C-C-C=C B) C=C-C-C=C-C=C-C C) C=C=C-C-C-C-C-C D) C-C=C-C-C=C-C-C E) C-C=C-C=C-C-C-C

A

Which molecule represents 4-ethyl-2-hexyne? Question 10 options: A) (CH3CH2)2CHC≡CCH3 B) CH3CH2C≡CCH2CH2CH3 C) CH3CH2CH2CH2C≡CCH3 D) (CH3CH2)2CHC≡CCH(CH2CH3)2 E) CH3CH2CH2C≡CCH3

B

Which of the following alkenes can exhibit cis-trans isomerism? Question 32 options: A) 2-methyl-2-octene B) 3-octene C) 1-pentene D) 1,1-dibromobutene E) none of these

D

Which of the following compounds is a saturated hydrocarbon? Question 30 options: A) benzene B) acetylene C) 1,3-butadiene D) hexane E) ethylene

D

Which of the following is a correct description of the difference between a saturated and an unsaturated hydrocarbon? Question 29 options: A) Unsaturated hydrocarbons are flammable but saturated hydrocarbons are not. B) Saturated hydrocarbons are essentially water insoluble while unsaturated hydrocarbons are water soluble. C) Saturated hydrocarbons are composed of carbon and hydrogen but unsaturated hydrocarbons include atoms other than carbon and hydrogen. D) Saturated hydrocarbons do not contain multiple bonds between carbons but unsaturated hydrocarbons do contain multiple bonds.

D

Which of the following is not the common name of an aromatic compound? Question 60 options: A) phenol B) xylene C) toluene D) acetone E) aniline

B

Which of the following reactions involves addition of two different elements to an alkene? Question 14 options: A) hydrogenation B) hydrohalogenation C) chlorination D) bromination E) none of the above

C

Which phrase most accurately describes the structure common to all aromatic compounds? Question 23 options: A) a six-membered ring with easily broken carbon-carbon bonds B) a ring described as 1,3,5-hexatriene C) identical bonds between all 6 carbon atoms, with 6 electrons moving freely D) a six-membered ring with 3 double and 3 single bonds E) none of the above

D

Which reactant should be used to convert propene to 1,2-dichloropropane? Question 62 options: A) BrCl B) NaCl C) H2 D) Cl2 E) HCl

B

Which reactant should be used to convert propene to 2-chloropropane? Question 18 options: A) NaCl B) HCl C) Cl2 D) BrCl E) H2

Naphthalene

_____ is familiar for its use in mothballs, is the simplest and best-known polycyclic aromatic compound

Addition

______ reaction is a general reaction type in which a substance X—Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Benzapyrene

_______ contains five benzene-like rings joined together; ordinary graphite (the "lead" in pencils) consists of enormous two-dimensional sheets of benzene-like rings stacked one on top of the other.

Halogenation

_______ is the substitution of a halogen group, X, for a hydrogen on an aromatic ring.

Sulfonation

_______ is the substitution of a sulfonic acid group, SO3H, for a hydrogen on an aromatic ring.