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  41)What is the major product of the following Friedel-Crafts alkylation? A)I B)II C)III D)IV E)V 42)What is the major organic product of the reaction between benzene and isobutyl chloride in the presence of AlCl3? A)tert-butylbenzene B)isobutylbenzene C)n-butylbenzene D)chlorobenzene E)sec-butylbenzene 43)What is the product of the following reaction?   Ethylbenzene     +    .
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  41)Provide the major organic product of the following. 42)When compound X is heated, PhC(=O)CH(CH3)2 and CO2 are produced. Offer a structure for compound X. 43)What product results when a malonic ester is treated with the following sequence of reagents? 1)NaOCH2CH3; 2)PhCH2Br; 3)H3O+, Δ? 44)What alkyl bromide should be used in the acetoacetic ester.
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21)Which of the following are considered to be bending (in-plane) vibrations? A)scissoring and wagging B)scissoring and twisting C)rocking and wagging D)rocking and twisting E)scissoring and rocking 22)Which of the following frequencies corresponds to the region where one would find the stretching frequency for a C=C in an IR spectrum? A)3650-3200.
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31)Which of the following is not a nucleophile? A)CH3NH2 B)PH3 C)+CH3 D) E) 32)What is the nucleophile in the reaction shown below? A)I B)II C)III D)IV E)V 33)Which of the following is the strongest nucleophile in an aqueous solution? A)HO- B)F- C)Cl- D)Br- E)I- 34)What is the definition of "nucleophilicity"?.
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21)Provide the structure of the major organic product of the following reaction. 22)Which of the following alcohols is oxidized to a ketone by chromic acid? A)I B)II C)III D)IV E)V 23)Which of the following reagents can be used to oxidize 1° alcohols to aldehydes? A)KMnO4 B)MnO2 C)K2Cr2O7 D)H2O2 E)PCC 24)What is.
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41)Why, in a polar protic solvent, is iodide a better nucleophile than fluoride? 42)Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide? A)These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom. B)Methoxide is more nucleophilic because.
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  11)Provide the proper IUPAC name for the compound below. 12)Provide the proper IUPAC name for ClCH2CH2CONHCH3. 13)Provide the proper IUPAC name for the compound below. 14)Provide the IUPAC name for the organic compound below. 15)Provide the IUPAC name for the organic compound below. 16)Provide the IUPAC name for the organic.
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81)Draw all likely alkene products in the following reaction and circle the product you expect to predominate. 82)Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-pentene as the only alkene product? A)1-chloropentane B)2-chloropentane C)3-chloropentane D)1-chloro-2-methylbutane E)1-chloro-3-methylbutane 83)Supply the missing alkyl.
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  11)Which of the following is aromatic? A)cyclopentadienyl cation B)1,3-cyclohexadiene C)cyclobutenyl anion D)1,3,5-hexatriene E)cycloheptatrienyl cation 12)Which of the following compounds is aromatic? A)I B)II C)III D)IV E)V 13)Which of the following is aromatic? A)I B)II C)III D)IV E)V 14)What is the name of the following structure? 15)What is the name.
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31)Provide the major organic product of the following. 32)In the chromic acid oxidation of alcohols, the chromium is __________. A)reduced from Cr+6 to Cr+3 B)oxidized from Cr+6 to Cr+3 C)reduced from Cr+3 to Cr+6 D)oxidized from Cr+3 to Cr+6 E)none of the above 33)What series of synthetic steps could be.
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31)Which compound would be expected to show intense IR absorption at 2710 and 1705 cm-1? A)CH3C(=O)CH2CH3 B)PhC(=O)CH3 C)PhCHO D)CH2?CHC(=O)CH3 32)Which compound would be expected to show intense IR absorption at 2250 cm-1? A)CH3CH2CH2CO2H B)CH3CH2CH2CN C)CH3CH2CH2CH2OH D)CH3CH2CH2CONH2 33)Which has a lower characteristic stretching frequency, the C-H or C-D bond? Explain briefly..
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11)Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation. CH3(CH2)6CH2OH + HBr → 12)Provide the structure of the major organic product in the reaction below. 13)Name and provide the structure of the major organic product which results when (R)-3,3-dimethyl-2-butanol is heated in.
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  31)Provide a synthesis of 2-ethylhexanol using butanal as the only source of carbon. 32)What is the major product for the following reaction? 33)What is the major product of the following condensation? A)I B)II C)III D)IV E)V 34)Provide the structure of the Claisen product in the self-condensation of methyl phenylacetate. 35)Show how.
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  31)Which of the following compounds is hydrolyzed most slowly in aqueous NaOH? A) B) C) D) E) 32)Acetyl chloride undergoes nucleophilic substitution at a faster rate than methyl acetate because __________. A)the ester is more sterically hindered than the acid chloride B)the acid chloride is more sterically hindered than the.
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  21)Provide the structure of benzenesulfonic acid. 22)Why does benzene undergo electrophilic substitution rather than electrophilic addition? 23)Discuss the role of benzene in the first step of an electrophilic aromatic substitution reaction. 24)Describe how the aromatic character of the benzene ring is re-created from the nonaromatic carbocation intermediate during an electrophilic.
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11)Which of the following normally occurs in a molecule when a photon of infrared light is absorbed? A)An electron moves to an orbital of higher potential energy. B)The vibrational energy increases. C)An electron changes alignment in a magnetic field. D)The molecule gains an electron. E)The molecule loses an electron. 12)What.
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71)Which of the following are the elimination products of the reaction shown below? CH3CH2Br + -OH → ? A)CH3CH2Br  +  H + O- B)HOCH2CH2Br C)CH3CH2OH  +  Br- D)CH2?CH2 + Br- +  H2O E)CH2?CHBr  +  H2O 72)Draw the alkene product which results when 1-bromopentane is heated in acetone containing NaOH. Give a.
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101)Why is E1 not a likely mechanism when 1-chloropentane is heated in ethanol? 102)Which of the following is least likely to be found in the product mixture which results when 2-iodopentane reacts with sodium ethoxide in ethanol? A)1-ethoxypentane B)2-ethoxypentane C)(Z)-2-pentene D)(E)-2-pentene E)1-pentene 103)What is the major product which results when.
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  61)Which of the following is (are) formed in the reaction between ethyl butanoate and ethyl amine? A)ethanol B)1-butanol C)N-ethylbutanamide D)both A and C E)both B and C 62)Provide the major organic product of the following: 63)Predict the major organic product of the reaction between N-methylbenzamide and sodium propanoate. A)N-propylbenzamide B)propyl.
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  51)Provide the best name for the organic compound below. 52)Provide the best name for the organic compound below. 53)Which of the following compounds reacts most slowly during nitration? A)I B)II C)III D)IV E)V 54)Which of the following compounds reacts most rapidly during nitration? A)I B)II C)III D)IV E)V 55)Which.
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41)Which of the following is the leaving group of an amine? A)OH B)NH2- C)COOH D)NH3 E)NH4+ 42)Which of the following is diisopropyl ether? A)CH3CH2CH2-O-CH2CH2CH3 B) C) D) E)none of the above 43)Which of the following is the correct structure for 2-isopropoxy-4-ethylheptane? A) B) C) D) E) 44)Draw all ethers with a molecular formula of C4H10O. 45)What are.
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  21)Which of the following is the correct ranking in decreasing order of relative Boiling Point of carbonyl containing compounds? A)primary amide > carboxylic acid >> ester ~acyl chloride ~ aldehyde ~ ketone B)ester > carboxylic acid >>  amide~acyl chloride ~ aldehyde ~ ketone C)aldehyde ~ ketone > carboxylic acid >>.
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1)Which of the following compounds does not have an alpha hydrogen? A)I B)II C)III D)IV E)all of the above 2)Draw an arrow pointing to the ?-carbon in the following molecule: 3)Describe what is meant by an alpha hydrogen. 4)List the following carbonyl compounds in order of decreasing pKa: 2,4-pentanedione, diethyl malonate,.
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51)Which of the following spectroscopic techniques uses the lowest energy of the electromagnetic radiation spectrum? A)UV B)visible C)IR D)X-ray E)NMR 52)Which of the following is used in nuclear magnetic resonance spectroscopy? A)X-ray B)infrared C)visible D)radio E)ultraviolet 53)If the frequency for flipping an 1H nucleus at an applied field of 1.4092.
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91)Which of the following statements is true concerning the E2 reactions of alkyl fluorides? A)Alkyl fluorides react more readily in E2 reactions than do alkyl iodides. B)The transition state of this E2 reaction resembles a carbanion rather than an alkene. C)The C-F bond is the weakest carbon-halogen bond so SN2.
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21)Which of the following does not provide evidence that there are two different mechanisms for nucleophilic substitution? A)reaction products when CH3I is used as the substrate B)reaction products when (CH3)3CCH2I is used as substrate C)the stereochemistry of nucleophilic substitutions D)the effect of nucleophile concentration on rate 22)Draw and describe the.
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  51)Give a detailed, stepwise mechanism for the Fischer esterification of acetic acid with methanol. 52)Which of the following conditions will drive the equilibrium of the Fischer esterification towards ester formation? A)addition of water B)removal of water as it is formed C)addition of an inorganic acid as a catalyst D)addition of.
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1)Describe what mass spectrometry allows you to determine. 2)Describe what can be determined from an infrared spectrum. 3)Describe what can be determine from nuclear magnetic resonance spectroscopic data. 4)Which statement(s) describes the base peak in a mass spec? A)a peak with a small m/z value. B)the tallest peak C)the atomic.
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51)What is the major product from the following reaction? A)I B)II C)III D)IV E)V 52)What is the major product for the following reaction? A)I B)II C)III D)IV E)V 53)What is the major product for the following reaction? A)I B)II C)III D)IV E)V 54)Provide the major organic product in the reaction below. 55)Provide the.
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111)Predict the two most likely mechanisms which occur when 2-iodohexane is heated in ethanol. A)SN2 and SN1 B)E1 and E2 C)SN2 and E2 D)E1 and SN1 E)E2 and SN1 112)Which base, ammonia (NH3) or triethylamine [(CH3CH2)3N], would be a better choice for use in converting 1-chlorohexane to 1-hexene? Explain briefly..
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  61)List the following compounds in order of decreasing reactivity toward electrophilic aromatic substitution: toluene, benzene, fluorobenzene, nitrobenzene, phenol. 62)Which of the following substituents acts as a moderate activator and o/p director in electrophilic aromatic substitution reactions? A)-Br B)-SO3H C)-CO2H D)-NHC(=O)R E)-CHO 63)Which of the following structures is the most important.
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61)Describe a hydrate and explain how it gets formed. 62)What is the major product of the following reaction which is takes place in the presence of an acid catalyst? A) B) C) D)No Reaction E) 63)Provide the structure of the hydrate of cyclopentanone. 64)The compound: can form a hemiacetal by reacting with itself in solution..
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  11)Rank the following compounds in order of increasing acidity of their ?-H's, least acidic to most acidic:  CH3CH2C(=O)N(CH3)2, PhC(=O)CH2CHO, CH3CH2CO2CH2CH3, and PhC(=O)CH2CO2CH2CH3. 12)When compared to the keto form, the enol form of which of the following compounds is most stable? A)I B)II C)III D)IV E)V 13)Which of the following is the.
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  41)In the lab, a student tried to prepare N,N-diethylacetamide by heating acetyl chloride with two equivalents of triethylamine. Was the student successful? Explain. 42)When benzoyl chloride is reacted with ammonia to prepare benzamide, two equivalents of ammonia must be used. Explain why this is the case. 43)Provide the major organic.
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41)Which compound would be expected to show intense IR absorption at 3300 cm-1? A)CH3CCCH3 B)butane C)1-butene D)CH3CH2CCH 42)Which of the following species has a characteristic absorption at 3300 cm-1 in its IR spectrum? A)(CH3)2CHCCH B)(CH3)2CHN(CH3)2 C)(CH3)2CHCCCH3 D)(CH3)2CHCH=CH2 E)(CH3)2CHCO2CH3 43)Which of the following functional groups will exhibit no IR absorption at.
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1)Which of the following compounds is an amide? A)I B)II C)III D)IV E)V 2)Which of the following compounds is an acyl chloride? A)I B)II C)III D)IV E)V 3)Which of the following compounds is an ester? A)I B)II C)III D)IV E)V 4)What is the common name for the following compound? A)λ-Chlorobutanoic acid B)β-Chlorobutanoic acid.
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1)What is the functional group in an alcohol? A)carbon-carbon double bond B)NH2 C)OH D)halogen E)COOH 2)Which of the following compounds does not have the molecular formula C6H14O? A)1-hexanol B)2-hexanol C)3-methyl-2-pentanol D)3-methyl-3-pentanol E)cyclohexanol 3)What is the IUPAC name for the following structure? A)4-sec-hexyl-5-methyl-3-hexanol B)3-hydroxy-4-isobutyl-5-ethyloctane C)5-ethyl-4-isopropyl-3-octanol D)3-hydorxy-4-isobutyl-5-propylheptane E)3-propyl-4-isopropyl-5-heptanol 4)Give the IUPAC name for.
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11)Which of the following SN2 reactions is the slowest? A)CH3CH2CH2Br + HO- → CH3CH2CH2OH + Br- B)CH3CH2CH2Cl + HO- → CH3CH2CH2OH + Cl- C)CH3CH2CH2I + HO- → CH3CH2CH2OH + I- D)CH3CH2CH2F + HO- → CH3CH2CH2OH + F- E) 12)Provide a detailed, stepwise mechanism for the reaction below. (CH3)2CHCH2CH2CH2I + CN-.
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1)Which of the following is not correct concerning substitution and elimination reactions of alkyl halides? A)The electrophile replaces the leaving group. B)Compounds containing electron-donating groups bonded to an sp3 hybridized carbon undergo substitution and elimination reactions. C)The electronegative atom is replaced by another atom or group in substitution reactions. D)A.
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41)Provide the major organic product of the following: 42)Which of the following alcohols can be prepared by the reaction of methyl formate with excess Grignard reagent? A)1-pentanol B)2-pentanol C)3-pentanol D)2-methyl-2-pentanol E)3-methyl-3-pentanol 43)Which of the following is correct? A)When a Grignard reagent reacts with a ketone, the addition product is a.
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51)What is the major organic product of the following reaction? A)I B)II C)III D)IV E)V 52)What is the major organic product of the following reaction? A)I B)II C)III D)IV E)V 53)Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine. 54)Provide a detailed, stepwise mechanism for.
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11)Provide the proper IUPAC name for PhCH2CH(CH3)CH2CH2CHO. 12)Provide the IUPAC name for the organic compound below. 13)Provide the IUPAC name for the organic compound below. 14)Would you expect the carbonyl carbon of benzaldehyde to be more or less electrophilic than that of acetaldehyde? Explain using resonance structures. 15)Which carbonyl is more.
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  31)Which of the following is the first step in the mechanism of bromination? A)I B)II C)III D)IV E)V 32)Provide a detailed, stepwise mechanism for the reaction of benzene with Br2 and FeBr3. Make sure to include the activating reaction between Br2 and FeBr3 in your mechanism.  33)Bromination of benzene requires a.
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