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83 Cards in this Set

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2) Polyethylene is a common organic polymer with many commercial applications. It has a very
large but simple structure consisting of hundreds or thousands of -CH2- units strung together.
This repeating unit is known as
a) a methyl group b) a methylene group c) an ethylene group d) a carbhydryl group
b) a methyene group
4) Which compounds on the list below are isomers?
A. Methylcycloheptane B. 1,1,3-Trimethylcyclopentane
C) 2,4-Dimethylhexane D. 1,3-Dimethylcyclopentane
a) A, B b) A, D c) B, C, D d) A, B, D e) A, B, C
A) A, B
5) Which of the following elements does this electron configuration represent? 1s22s22p4
a) F b) C c) N d) Cl e) O
e) O
7) What are the products formed from the following acid-base reaction?
CH3OH + NH3 ⎯→
a) CH3O- + NH4+ b) CH2OH + NH4+ c) CH3OH2+ + -NH2
d) CH3NH2 + H2O e) CH4 + NH2OH
A) CH3O- + NH4+
8) Which of the following is closest to the C-O-C bond angle in CH3-O-H?
a) 180° b) 120° c) 109.5° d) 90° e) 60°
c) 109.5
9) What is the predicted shape, bond angle, and hybridization for +CH3, the methyl carbocation?
a) Trigonal planar, 120°, sp2 b) Trigonal planar, 120°, sp3
c) Tetrahedral, 109.5°, sp3 d) Trigonal pyramidal, 120°, sp2
e) Trigonal pyramidal, 109.5°, sp3
A) trigonal planar, 120, sp2
10) In the compound methylamine, CH3NH2, which of the following best describes the true charge on the nitrogen atom?
a) +1 b) slightly positive c) uncharged d) slightly negative e) –1
D) slightly negative
12) If an alkene that contains one ring and one double bond has n carbon atoms, how many hydrogen atoms must it also contain?
a) n b) n+2 c) n-2 d) 2n e) 2n+2 f) 2n-2
F) 2n-2
13) Hexane is a common organic solvent. It burns in a combustion (oxidation) reaction just as all hydrocarbons do. How many moles of carbon dioxide are produced when one mole of hexane reacts?
a) 1 b) 3 c) 6 d) 8 e) 12
C) 6
7) Name the two types of strain that account for the energy difference between the least stable and most stable conformations of butane.
torsional and steric
10) For ethanol, CH3CH2OH, give the formula for its conjugate acid.
CH3CH2OH2+_
11) The approximate pKa of an typical alcohol is
15-18
12) A certain hydrocarbon has an empirical formula of CH2. Its molar mass is about 140 g/mol. What is the molecular formula of this compound?
Empirical formula weight is 14 g/mol. Therefore 140/14 or 10 of the empirical formula units must be in the molecular formula, which is C10H20.
1) Cocaine, particularly in its basic form, is a highly addictive drug of abuse. It has the chemical formula C17H21NO4. When it is reacted with hydrogen gas and a metal catalyst like platinum or palladium, a new compound with the formula C17H31NO4 is formed. How many pi bonds and rings does cocaine have?
Pi bonds ____5______ Rings _____3______
4) A given compound has the molecular formula of C6H6. After being treated with hydrogen gas and a trace of palladium metal, a compound with the formula C6H12 is formed. How many pi bonds and how many rings were in the original material.
Pi bonds = 3

Rings = 1
2) Which of the following elements does this electron configuration represent? 1s22s22p4
a) F b) C c) N d) O e) Si
D) O
3) Identify the isomer of C6H14 that has only primary and secondary carbons.
a) hexane b) 2,2-dimethylbutane c) 3-methylpentane d) 2,3-dimethylbutane
A) hexane
6) Which of these chemical reactions is commonly carried out with alkanes?
a) cracking b) distillation c) hydration d) acid-base
A) cracking
8) Which of the following is closest to the C-C-O bond angle in (CH3)3CCOCH3 ?
a) 180° b) 120° c) 109.5° d) 90° e) 60°
B) 120
9) What class of compound is represented by the formula (CH3)3CCOCH3?
a) aldehyde b) ketone c) ether d) ester
B) ketone
10) Rank the following three compounds in order of increasing boiling point.
A. CH3CH2CH3 B. CH3CH2OH C. CH3OCH3
. a) A<B<C b) A<C<B c) B<C<A d) B<A<C
B) CH3CH2OH
11) Which of these formulas represent an alkyne?
a) CH3CH2CH2CN b) CH3CH2CCH c) CH3COCH2CH3 d) CH3CH2CH2CHO
B)
15) Which statement correctly describes the structure of BH3 and NH3?
a) both are trigonal planar b) both are pyramidal
c) BH3 is trigonal planar and NH3 is pyramidal
d) BH3 is pyramidal and NH3 is trigonal planar
C
16) An alkane with 13 carbons is most likely to show up in which of these?
a) gasoline b) diesel fuel c) lubricating oil d) asphalt
B) diesel fuel
17) What is the approximate O-C-C bond angle in CH3CH2COCH2CH3?
a) 180 b) 120 c) 109 d) can’t be determined
B) 120
18) Which of these compounds has the lowest boiling points?
a) CH3CH2CH2NH2 b) CH3CH2NHCH3 c) (CH3)N
d) must be determined experimentally
C)
4) A certain compound has a structural formula of (CH3)3C(CH2)3C(OH)2CH3. What is its molar mass? (4 pt)
Molecular formula is C9H20O2. Molar mass (integers) is 160 g/mol.
5) Which intermolecular force is responsible for the strongest attractions that exist between ester molecules? (3 pt)
dipole-dipole
6) For isopropanol, (CH3)2CHOH, give the formula of its conjugate acid __
(CH3)2CHOH2+
1) The conjugate base of a strong acid is always / sometimes / never a weak base (circle one).
always
2) True-false
____ Copying off someone else’s paper could result in an Honors F for the course.

____ A triple bond is composed of a 2 sigma bonds and a pi bond.

____ A silicon-silicon bond is relatively strong compared to a carbon-carbon bond.

____ An sp3 hybridized atom can have a bent molecular geometry.

____ Carbon makes up a little over 5% of the Earth’s crust.
T, f,f,t,f
1) Which of the following elements does this electron configuration represent? 1s22s22p3
a) F b) C c) N d) Cl e) O
c
4) Which of the following is most likely to have ionic bonds?
a) HCl b) SO2 c) H2S d) Na2O e) NCl3
d
5) The conjugate base of ammonia, NH3, is
a) NH2- b) NH2OH c) NH4+ d) NH4 e) NH2
a
6) Rank A through D in decreasing order of basicity.
A: CH3OCH3 B: CH3CH2NH2 C: CH3CH2O- D: CH3CH2-
a) D > C > B > A b) D > C > A > B c) D > B > A > C d) B > A > D > C
a
7) The eclipsed and staggered forms of ethane are said to differ in:
a) molecular formula b) configuration c) conformation d) constitution
e) structure
c
8) Which of the following is the most soluble in water?
a) CH3CH2OCH2CH3 b) CH3CH2CH2OH c) CH3CH2CH2Cl d) CH3CH2CH2CH3
e) CH3CH2CHO
b
9) Which of the following best explains the relative stabilities of the eclipsed and staggered forms of ethane? The ________ form has the most ________ strain.
a) eclipsed: steric b) eclipsed: torsional c) staggered: torsional
d) staggered: steric
b
11) Which of the molecules below have a net dipole moment?
A. CH3F B. CF4 C. BCl3 D. CH3OH
a) A,B b) A,C c) A,D d) A,B,D e) A,C,D
c
12) Which of these compounds would have the highest degree of angle (ring) strain?
a) cyclomethane b) cycloethane c) cyclopropane d) cyclobutane
e) cyclopentane
c
13) An acid with a pKa of 10 would be considered
a) very strong b) moderately strong c) weak d) very weak e) wimpy
c
7) Which intermolecular force is responsible for the attractions that exist between alkane molecules?
london dispersion
8) What factor determines whether a covalent bond is polar or nonpolar?
diffrences in electornegativities between the bonded atoms leads to polar bonds
9) Acetylsalicylic acid (aspirin) has a pKa of 3.48. Ascorbic acid (Vit C) has a pKa of 4.17. Acetic acid: 4.74; oxalic acid: 1.19; formic acid: 3.75. Which of these organic acids has the strongest conjugate base?
Acetic acid, since it’s the weakest acid
10) Circle the strongest acid in each group.
CH2ClCH2COOH CH3CHClCOOH CH3CH2COOH H2S SiH4 PH3

CH3COOH CH2ClCH2OH CH3CH2OH H2O H2Se H2S
CH3CHClCOOH
H2S
CH3COOH
H2Se
1) Multiple choice. (45 pts)
1) In a reaction energy diagram of a multistep reaction, which best describes the rate-determining step?
a) the step that involves the highest energy transition state
b) the first step
c) the step with the highest activation energy
d) the step leading to the products
e) the step leading to the highest energy intermediate
a
2) Which best describes the geometry and the C-hybridization of a radical center?
a) pyramidal, tetra-coordinated sp3 C-atom
b) planar, trigonal sp2 C-atom
c) pyramidal, tris-coordinated sp3 C-atom
d) pranar, trigonal sp C-atom
b
3) The major monobrominated product which results when ethylcyclohexane is subjected to free radical bromination is
a) a primary bromide b) a secondary bromide c) a tertiary bromide
d) a quaternary bromide e) a benzylic bromide
c
5) Which of these solvents could be described as polar and protic?
a) ethanol b) acetonitrile c) dimethylformamide d) acetone e) 18-crown-6
a
7) Which of the following statements about an SN1 reaction is correct?Spring 2010 doesn’t know this yet
a) It involves possible carbocation rearrangements.
b) It has a one step mechanism.
c) Primary alkyl halides are more reactive than tertiary alkyl halides.
d) The product has an inverted configuration compared to the configuration of the reactant.
e) It has a bimolecular rate-determining transition state.
a
8) In an SN1 reaction, the effect of doubling both nucleophile and substrate concentrations at the same time is to multiply the reaction rate by
a) ¼ b) ½ c) 0 d) 2 e) 4
d
10) How many distinct monochlorinated products will result when isobutane (2-methylpropane) is subjected to free radical chlorination?
a) 1 b) 2 c) 3 d) 4
b
12) Which description is most accurate for the carbon-chlorine bond of an alkyl chloride?
a) nonpolar; no dipole b) polar; δ+ at carbon, δ- at chlorine
c) ionic d) polar; δ+ at chlorine, δ- at carbon
b
13) Which compound will undergo an SN2 reaction most readily?
a) (CH3)3CCH2I b) (CH3)3CCl c) (CH3)2CHI
d) (CH3)2CHCH2CH2CH2I e) (CH3)2CHCH2CH2CH2Cl
d
14) Which of the following is a carbene?
a) CH2=CHO-- b) CH3CH2. c) Cl2C: d) Cl3C:-- e) CH3CH2+
c
15) For a given reaction, if ΔG is greater than zero, then
a) Keq < 0 b) Keq = 0 c) 0 < Keq < 1 d) Keq = 1 e) Keq > 1
c
1) What is the number of unsaturations (pi bonds and rings) in a molecule with the formula C5H6N2O2?
a) 0 b) 1 c) 2 d) 3 e) 4
e
4) Which of the following alkyl halides would form the greatest yield of 2-pentene as a result of reaction with methoxide ion?
a) 1-bromopentane b) 2-bromopentane c) 3-bromopentane d) 4-bromopentane
e) 5-bromopentane
c
5) Which of the following statements about an E2 reaction is not correct?
a) It does not involve carbocation rearrangements.
b) It has a one step mechanism.
c) Primary alkyl halides give better yields of elimination product than tertiary alkyl halides.
c) It is favored by strong, bulky bases.
d) It has a bimolecular rate-determining transition state.
c
10) A certain reaction is first order for each of the two reactants. If the concentration of one reactant was doubled and the other was cut in half, the reaction rate for the resulting reaction would
a) double b) be unchanged c) quadruple d) be cut in half
b
11) Which is a correct name?
a) 1-ethyl-1-pentene b) 2-methylpentene c) 5-chloro-3-hexene d) 4-hexene
e) 5-bromo-2-pentene
e
12) A compound C20H32 can be hydrogenated with platinum and hydrogen to compound C20H38. How many double bonds, DB, and rings, R, does the original compound have?
a) 3 DB, 2 R b) 3 DB, 3 R c) 2 DB, 2 R d) 2 DB, 3 R e) 4DB, 1R
a
14) Which of the following is the best reaction to use to accomplish an anti-Markovnikov addition of water to an alkene?
a) water + dilute acid b) halogenation c) hydroboration-oxidation
d) oxymercuration-demercuration e) catalytic hydrogenation
c
15) Which of the following statements best describes the relative bond dissociation energies of the sigma and pi bonds present in the carbon-carbon bond of an alkene?
a) sigma > pi b) pi > sigma c) pi = sigma d) it varies
a
12) Which of the following is the best reaction to use to form an ether?
a) catalytic hydrogenation b) water + dilute acid c) hydroboration-oxidation d) alkoxymercuration-demercuration e) oxymercuration-demercuration
Ans: d Adds alcohol across a double bond.
14) How many isomeric alkenes of the formula C5H10 are possible, including stereoisomers?
a) three b) four c) five d) six e) seven
d
15) Which of the following is the experimentally determined rate expression for an E1 reaction?

a) Rate = k[R-X] b) Rate = k[R-X]2 c) Rate = k[R-X][base] d) Rate = k[base]
Ans: a First order elimination
18) What is the major product of the following reaction? Ans: c
CH3CH2CH2CH=C(CH3)2 + Br2 -->

a) 1,2-dibromo-2-methylhexane b) 2,2-dibromo-2-methylhexane
c) 2,3-dibromo-2-methylhexane d) 2,4-dibromo-2-methylhexane
c
4) Fluorouracil is a derivative of one of the nitrogenous bases found in RNA. It is used as an anticancer agent. It has the formula C4H3N2O2F. After hydrogenation, the formula becomes C4H9N2O2F. How many pi bonds and how many rings does fluorouracil have? Show work. (4 pt)
_____3____ pi bonds



_____1____rings
1) A newly isolated natural product was found to have the molecular formula C15H28O2. By hydrogenating a sample of the compound, it was determined to possess one pi bond. How many rings are present in the compound?
a) 0 b) 1 c) 2 d) 3 e) 4
b
2) Which alkene will not rearrange in the course of an electrophilic addition?
a) 3,3-dimethyl-1-butene b) 3-ethylcyclohexene c) 3-methyl-2-hexene d) vinylcyclopentane
c
3) The Simmons-Smith reaction involves an intermediate that is a
a) cyclic cation b) a carbanion c) a carbenoid d) a radical
c
5) Which of the following alkyl chlorides will undergo SN1 reaction most readily?
a) 1-chloro-4-methylpentane b) 2-chloro-4-methylpentane
c) 2-chloro-3-methylpentane d) 3-chloro-2-methylpentane
e) 2-chloro-2-methylpentane
e
6) When (Z)-3,4-dimethyl-3-hexene is reacted with hydrogen gas and a Raney nickel catalyst, what
product(s) will form?
a) a meso form b) a racemic mixture c) an optically active solution
d) a mixture that contains no chiral carbons
a
10) Which of the following species is the least nucleophilic?
a) H2O b) BF3 c) (CH3)3N d) CH3O- e) CN-
ans: b (a is acceptable)
15) Dehydration of an alcohol is essentially what type of reaction
a) E1 b) E2 c) SN1 d) SN2 e) electrophilic addition
a
16) Which of the following is the best reaction to use to accomplish an anti-Markovnikov addition of water to an alkene?
a) water + dilute acid b) halogenation c) hydroboration-oxidation
d) oxymercuration-demercuration e) catalytic hydrogenation
c
4) A compound with the formula C6N2H7ClO2 was treated with hydrogen gas over a Raney nickel catalyst and a new material, C6N2H13ClO2, was formed. How many pi bonds and/or rings did the original compound have? (4 pt)
π bonds = 3

rings = 1
2) When an aldehyde is reacted with an alkyl lithium compound, after acid hydrolysis the result is
a) a ketone b) a primary alcohol c) a secondary alcohol d) a tertiary alcohol
c
4) Which alkyne below would give two different ketones in approximately the same amount with the H2SO4 / Hg2+ catalyzed addition of water?
a) cyclodecyne b) 4-decyne c) 1-decyne d) 5-decyne
b
7) Which reagent below would be used to convert pent-2-yne into trans-pent-2-ene?
a) NaNH2 / NH3 b) H2 / Lindlar Pd c) Na / NH3 d) H2O / HgSO4 / H2SO4
c
8) What is the relationship between the keto and enol forms of acetone (CH3COCH3)?
a) resonance structures b) diastereomers c) different conformations d) constitutional isomers
a
10) The greater acidity of terminal alkynes as compared with alkanes is primarily attributed to
a) the greater electronegativity of sp hybridized carbons compared to sp3 hybridized carbons
b) the lower electronegativity of sp hybridized carbons compared to sp3 hybridized carbons
c) the π electrons stabilizing the negative charge
d) the π electrons destabilizing the negative charge.
a