CH 221: FINAL EXAM
82 Cards in this Set
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Name the functional group: R-OH
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alcohol
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Name the functional group: R-X
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alkyl halide
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Name the functional group: R-N2
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amine
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Name the functional group: Oxygen bonded to two carbon R groups
hint: makes a ring
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epoxide
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Name the functional group: R-O-R
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ether
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Name the functional group: R-C(triple bond)N
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nitrite
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Name the functional group: R-NO2
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nitroalkane
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Name the functional group: R-SH
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thiol
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Name the functional group: Ch3CH2C(double bond)OH
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aldehyde
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Name the functional group: CH3CH2COCH3
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keytone
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Name the functional group: CH3CH2COOCH3
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ester
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Name the functional group: CH3CH2COOH
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carboxylic acid
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(Comparing isomers) When an alkane has more branches the boiling point is ________ than a straight alkane chain.
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lower (the more branched, the more stable, the less heat of combustion, the lower the PE)
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Different spatial arrangements of a molecule that are generated by rotation about single bonds
Conformational Isomers
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Conformational Isomers
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Gauche
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The relationship between two atoms or groups whose dihedral angle is more than 0 degrees (i.e., eclipsed) but less than 120 degrees
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Eclipsed
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two substituents on adjacent atoms are in closest proximity, implying that the torsion angle is 0°
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Anti
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Most stable, dihedral angle of 180 degrees, two substituents on adjacent atoms are the farthest apart they could be (no VDW strain)
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General rule: the bulkier the substituent, the more favored the the conformation with it in the _________ position (referring to chair conformation of cyclohexane)
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equatorial
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True or False: Alkyl groups are bulkier than halogens.
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True
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Compounds that have the same molecular formula and different connectivity
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Constitutional Isomers
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If you have tran-1,4-dibromocycloheane, would the axial or equatiorial position be more stable?
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Equatorial
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In a reaction, the _______ energy side is always more favored at equilibrium.
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lower
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The smaller the pKa, the ______ the acid
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stronger
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The bigger the halogen, the _______ the boiling point
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higher
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Alcohol has a _______ boiling point than an alkyl halide except for an alkyl iodide (propyl iodide and beyond)
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higher
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Predict the major product and name the type of reaction:
R-OH+HBr----->
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R-Br + H2O
alcohol to alkyl halide
can occur with primary (SN2), secondary, or tertiary ROH (SN1)
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Predict the major product and name the type of reaction:
R-OH+HCl----->
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R-Cl +H2O
alcohol to alkyl halide
can occur with tertiary ROH (SN1)
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Predict the major product and name the type of reaction:
R-OH+PBr3----->
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R-Br +H3PO3
alcohol to alkyl halide
can occur with primary and secondary ROH (SN2)
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Predict the major product and name the type of reaction:
R-OH+SOCl2,base ----->
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R-Cl+HCl+SO2
alcohol to alkyl halide
can occur with primary and secondary ROH
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Predict the major product and name the type of reaction:
R-H+Cl2, hv ------->
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R-X (all H equivalent)
alkane to alkylhalide- free radical
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Predict the major product and name the type of reaction:
R-H+Br2, hv ------->
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R-X (uses tertiary C)
alkane to alkylhalide- free radical
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True or False: Deuterium shows up in NMR spectroscopy.
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False
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Name this reaction:
alcohol + H2SO4, heat-----> alkene
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E1 (regio- and stereoselective, so rearrangements can occur)
Stereoisomers can be produced, but trans- favored
dehydration of alcohol
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alcohol + sodium ethoxide, ethanol ------> alkene
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E2 (no rearrangements)
dehydration of alcohol
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List the leaving groups in order from slowest rate to fastest:
RF, RBr, RF, RCl
RF<<RCl<RBr<RI
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RF<<RCl<RBr<RI
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What results when using dilute H2SO4 on an alkene?
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The -OH bonds on the least substituted carbon
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Free redical addition of HBr results in __________ addition, while HBr, ROOH with perioxides results in __________ addition.
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Markovnikov, anti-Markovnikov
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When an alkene reacts with H2 to make an alkane
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Hydrogenation (hydration)
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When an alkene reacts with Br2, what is the major product?
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A vicinal dihalide (Br are anti-)
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What is produced when an alkene reacts with Br2 and H2O?
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a vicinal halohydrin
it is regioselective for Markovnikov alcohol and anti-Markovnikov Br
will bond anti- on a cyclo- ring
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When H2 reacts with a metal catalyst, there is a stereospecific reaction resulting in ____ addition of the Hydrogens.
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Syn (there will be stereoisomers)
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When an alkene reacts with Br2 or Cl2 in cold and dark conditions, the two halogens bond _____ to each other.
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anti
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each pair of molecules that are mirror images of each other
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enantiomer
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two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent (related) stereocenters and are not mirror images of each other.
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diastereomer
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a molecule with multiple stereocenters that is superimposable on its mirror image
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meso compound
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a sample that contains both enantiomers in equal amount is said to be optically ________
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inactive
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If there is no enantiomer there is a net reaction, so the sample is said to be optically _______ and optically ___________.
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active; pure
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SN2 is stereospecific: the nucleophile attacks from the _____ while the leaving group leaves from the _____.
The stereospecific consequence when the attacked carbon is chiral, there will be __________________________.
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back, front
an inversion of configuration (provided that the priority leaving group and the nucleophile have the same priority ranking)
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For NMR what groups are present at these ppms?
a) mid-high 3s
b) between 4-5
c) between 6-8
d) around 10
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a) halogen or oxygen
b) alkene
c) benzene ring
d) aldehyde H
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The formula for maximum stereoisomers
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2^n
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carbocation intermediate creates __________.
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racemates
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Epoxide ring opening:
under basic conditions, the __________________ site will be attacked
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least hindered
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Epoxide ring opening:
under acidic conditions, the ________________ side will be attacked
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more substituted
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True of False: When two substituents are cis- in the alkene state, when reacted to form an epoxide, the substituents will remain cis-.
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True
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Hydrogenation (with a metal catalyst) of an aldehyde (HCOR) will yield a(n)
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primary alcohol
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A Grignard reagent reacting with formaldehyde (HCOH) will yield (after an aqueous workup) a(n)
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primary alcohol
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A primary alkoxide treated with a primary alkyl bromide, but not heated, will yield a(n)
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ether
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Lithium aluminum hydride (LiAlH4) will convert a ketone (after an aqueous workup) to a(n)
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secondary alcohol
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The only reagent listed in the table above that will react with diethyl ether is
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HBr
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halides on adjacent carbons
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vicinal dihalide
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two halides on the same carbon
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geminal dihalide
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When making an alkene from an alkyne, syn addition only give the _____ stereoisomer
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cis-
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(Alkynes)
when using H2, Lindlar, Pd there is a ____ alkene formed as a product
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cis-
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(Alkynes)
when using XS, H2, Pd, the resulting product is an ________
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alkane
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(Alkynes)
when using 2Na, 2NH3, there is a ______ alkane formed as a product
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trans-
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each of two or more isomers of a compound that exist together in equilibrium, and are readily interchanged by migration of an atom or group within the molecule
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tautomer
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interconversion of isomers by a proton transfer and a double bond shift
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tautomerism
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In ozonolysis of alkynes, terminal alkenes produce ________ and ________.
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carboxylic and carbonic acid
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Whenever you see 9 or a multiple of 9 in the integration ratio, which group should you first consider for being responsible for that signal?
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tert-butyl
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Whenever you see a quartet and triplet on a spectrum, which group should you first consider for being responsible for those signals?
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ethyl
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Whenever you see septet and a doublet on a spectrum, which group should you first consider for being responsible for those signals?
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isopropyl
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Whenever you see 6 or a multiple of 6 in the integration ratio, which group should you first consider for being responsible for that signal?
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isopropyl
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Whenever you see 3 as the actual number of protons for a given signal, which group should you first consider for being responsible for that signal?
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methyl
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Alkyne Reactions: predict the product
alkyne + Na, NH3 ----------->
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trans-alkene
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Alkyne Reactions: predict the product
alkyne + HgSO4, H2SO4 ----------->
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keytone
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Alkyne Reactions: predict the product
alkyne + HX ----------->
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vinyl halide
no peroxides: Markovnikov
peroxides: anti-Markovnikov
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Alkyne Reactions: predict the product
alkyne + 2HX ----------->
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geminal halide
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Alkyne Reactions: predict the product
alkyne + X2 ----------->
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trans-dihaloalkene
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Alkyne Reactions: predict the product
alkyne + 2X2 ----------->
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tetrahaloalkane
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Alkyne Reactions: predict the product
alkyne + 1. O3, 2. H2O ----------->
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carboxylic acid
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Alkyne Reactions: predict the product
alkyne + 2H2, metal catalyst ----------->
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alkane
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Alkyne Reactions: predict the product
alkyne + H2, Lindlar Pd ----------->
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cis-alkene
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CH 221: TEST 2