Which of the Following Compounds Can Undergo an Aldol With Itself?
Aldehydes and Ketones
1. Which of the post-obit is a correct name for (CH3)2C=CHCOCH3?
A) ii-methyl-two-penten-4-1
B) 4-methyl-iii-penten-ii-one
C) ane,3-dimethyl-two-pentenal
D) isopentenone
ii. Which of the post-obit is 3,3-diphenylpropanal?
A) C6HfiveCHiiCH(C6H5)CHO
B) C6HvCHiiCHtwoCOC6H5
C) (Chalf dozenHv)iiCHCHiiCHO
D) (C6H5)2CHCH2COC6H5
3. Which of the following compounds is non named correctly?
| A) two-methyl-3-heptanone (CHiii)2CHCOCHtwoCH2CHiiCHthree |
| B) phenylacetaldehyde CviH5CHiiCHO |
| C) 4-hexyn-two-one CH3COCH2C≡CCH3 |
| D) para-bromoacetophenone p-BrChalf dozenH4CH2COCHthree |
4. Which of the following compounds is not named correctly?
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5. Which of the following compounds is not named correctly?
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6 Which of the following may be classified as an acetal?
A) I & Ii
B) III & IV
C) only 4
D) all but IV
vii Which of the following reactions is a skilful method for preparing an aldehyde?
A) Jones' reagent and a 1º-booze
B) Jones' reagent and a 2º-alcohol
C) PCC and a 1º-alcohol
D) H2And sofour a 1º-alcohol and oestrus
8 Which of the following are enol tautomers of iii-methylcyclohexanone?
A) I & II
B) I & Iv
C) 2 & III
D) but I
9 Which of the following statements is non more often than not truthful?
A) C=O is stronger than an equivalent C=C
B) C=O has a larger bond dipole than C=C
C) aldehydes and ketones have higher humid points than similarly sized alkenes
D) alkenes add nucleophiles more rapidly than aldehydes or ketones of similar structure
10 Which of the following compounds exchanges the largest number of hydrogens for deuterium when treated with KOD in DtwoO?
A) 3-methyl-1,two-cycloheptanedione
B) 2-methyl-1,three-cycloheptanedione
C) v-methyl-ane,3-cycloheptanedione
D) half dozen-methyl-one,4-cycloheptanedione
eleven Four C8H14O ketones are examined past 13Cnmr spectroscopy.
One of them has five singled-out carbon signals. Which of the following fits this fact?
A) 4,4-dimethylcyclohexanone
B) 3,3-dimethylcyclohexanone
C) 2,2-dimethylcyclohexanone
D) ii,two,4,four-tetramethylcyclobutanone
12 Which of the following compounds could non be converted to pentanal in one or two steps?
A) 1-pentyne
B) trans-5-decene
C) 2-pentanone
D) 1-pentanol
13 Treatment of cyclohexanone with an backlog of H2 18O produces eighteenO labeled cyclohexanone.
Which of the following is a likely intermediate in this isotope commutation? (the isotope is non named)
A) 1-cyclohexen-1-ol
B) one,1-cyclohexanediol
C) 2-cyclohexen-1-one
D) i,2-cyclohexanediol
14 Reaction of CviH5CHBr2 with NaOH in aqueous THF is likely to produce which product?
A) C6H5CHBrOH
B) C6HvCH(OH)2
C) Chalf-dozenH5CHO
D) CsixH5CO2H
fifteen Which of the following carbonyl compounds reacts virtually rapidly with nucleophilic reagents?
A) benzaldehyde
B) 3,3-dimethylbutanal
C) acetophenone
D) 2,2-dimethylcyclohexanone
sixteen Which of the following amines would be best called for preparing an enamine derivative from cyclohexanone?
A) dimethylamine
B) ethylamine
C) trimethylamine
D) hydroxylamine
17 Which reaction or sequence of reactions would best accomplish the post-obit synthesis?
A) CH3NHii, acid catalyst & heat
B) CH2=NH, acid goad & heat
C) (i) NH3 acrid goad & heat; (ii) CH2I2 & Zn(Cu)
D) (i) HCN & NaCN; (ii) LiAlH4 in ether
eighteen Heating cyclopentanone with either: I ethyl amine, or Ii diethylamine, together with an acid goad leads to unlike results.
Which of the following best describes this difference?
A) I gives an imine & II fails to react
B) I gives an enamine & II fails to react
C) I gives an imine & II gives an enamine
D) I gives an enamine & 2 gives an imine
19 Which reaction or sequence of reactions would be best used to convert cyclohexanone to cis-i,two-cyclohexanediol?
A) PCC in CHtwoCl2 and base of operations
B) (i) NaBHfour; (two) H3POiv & heat; (iii) OsO4 in pyridine
C) (i) NaBH4; (ii) H3PO4 & heat; (iii) CsixH5CO3H
D) (i) NaBH4; (ii) OsOfour in pyridine
20 A CnineHtenO chemical compound has a potent assimilation at 1686 -1cm in the infrared.
Which of the following compounds would exist expected to display such an assimilation ring?
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21 A CixH10O compound has a strong absorption at 1730 and two smaller but sharp absorption peaks at 2719 & 2818 -anecm in the infrared. The 1Hnmr has a strong doublet at δ1.0 ppm.
Which of the following compounds would be expected to display these features?
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22 The Wittig reaction takes place between a carbonyl chemical compound and a phosphorus ylid.
Which of the following represents the dipolar contributor to such an ylide?
A) I & II
B) Two only
C) Iii only
D) I & Iv
23 Which of the following reaction sequences would be best for converting cyclohexanol to methylenecyclohexane, (CH2)fiveC=CH2 ?
A) (i) H3PO4 & heat; (ii) CHiiI2 + Zn(Cu)
B) (i) PCC in CHtwoCltwo; (ii) CH3MgBr; (three) HiiiPOiv & oestrus
C) PCC in CHiiCl2; (ii) (C6H5)3P=CH2
D) CH2N2 & rut
24 Which of the following Wittig reagents would be useful for converting R2C=O into RiiCHCH=O?
A) (C6H5)3P=CH-OCHiii
B) (Chalf-dozenH5)3P=CH-CH3
C) (C6H5)3P=Cltwo
D) (CsixH5)3P=CH-CH=CHii
25 Two equivalents of the Wittig reagent (CH3)2C=CH-CH=P(C6H5)3 were immune to react with a CivHfourO2 chemical compound.
The primary product was ii,eleven-dimethyl-2,4,6,8,10-dodecapentaene, (CH3)2C=CH(CH=CH)3CH=C(CH3)2.
What was the C4H4O2 compound used in this reaction?
A) 2-butyne-one,4-diol
B) 1,two-cyclobutanedione
C) 1,3-butadien-2,iii-diol
D) 2-butenedial
26 Which of the following reactions would not be a useful manner of preparing 1-phenyl-2-butanol?
A) phenylacetaldehyde + ethylmagnesium bromide
B) butanal + phenylmagnesium bromine
C) propanal + benzylmagnesium bromine
D) 1-phenyl-ii-butanone + NaBHiv
27 Which of the post-obit reactions would not be a useful mode of preparing ii-phenyl-2-butanol?
A) two-butanone + phenylmagnesium bromine
B) acetophenone + ethylmagnesium bromide
C) cis-ii,iii-dimethyloxirane + phenylmagnesium bromide
D) ethylphenylketone + methylmagnesium iodide
28 In the reaction of (R)-3-phenyl-2-butanone with methylmagnesium iodide, what happens to the configuration of the stereogenic heart?
A) null, it remains unchanged
B) inversion takes place
C) racemization occurs
D) the product is achiral
29 Which of the following reactions would not be useful for converting four,4-diethylcyclohexanone into 1,1-diethylcyclohexane?
A) Wolff-Kishner reduction (N2H4, strong base of operations & heat)
B) Clemmensen reduction (Zn/Hg, acrid & heat)
C) thioacetal reduction (i HSCH2CH2SH & BFiii; 2 H2 + Raney Ni)
D) LiAlH4 in THF & heat
30 Which of the following is a semicarbazone derivative of an aldehyde (RCHO)?
A) RCH=N-NHCONH2
B) RCH=Northward-OH
C) RCH=N-NH2
D) RCH=N-C(CH3)3
31 Which of the post-obit isomers is most acidic ?
A) 3,4-hexanedione
B) 2,5-hexanedione
C) 2,4-hexanedione
D) hexanedial
32 You have ii C6H10O ketones, I and II. Both are optically active, simply I is racemized past treatment with base and II is not.
Wolff-Kishner reduction of both ketones gives the aforementioned achiral hydrocarbon, formula Chalf-dozenH12.
What reasonable structures may be assigned to I and Two?
A) I is three-methyl-4-penten-ii-ane; Ii is four-methyl-ane-penten-3-one
B) I is two-methylcyclopentanone; II is 3-methylcyclopentanone
C) I is 3-methylcyclopentanone; II is 2-methylcyclopentanone
D) I is ii-ethylcyclobutanone; II is iii-ethylcyclobutanone
33 Jones' reagent oxidizes aldehydes to carboxylic acids but normally does not oxidize ketones.
What intermediate species is most likely responsible for the aldehyde oxidation?
A) a carbonyl hydrate
B) an enol tautomer
C) an oxonium conjugate acrid of the aldehyde
D) an acylium cation
34 The lithium enolate base of operations from cyclohexanone reacts with alkyl halides, ofttimes in unlike ways.
As shown hither, methyl iodide and tert-butyl bromide react to give different organic products, I and Two, together with lithium halides.
What are the products from these reactions?
A) I is 2-methylcyclohexanone; II is two-t-butylcyclohexanone
B) I is 1-methoxycyclohexene; II is 1-t-butoxycyclohexene
C) I is ii-methylcyclohexanone; II is ane-t-butoxycyclohexene
D) I is ii-methylcyclohexanone; Two is a mixture of cyclohexanone and 2-methylpropene
35 A CvH12O compound is optically active, and is oxidized by PCC in CH2Cl2 to an optically active C5H1OO product, which is racemized in acrid or base.
Which of the following best fits these facts?
A) 2-pentanol
B) ii-methoxybutane
C) two-methyl-ane-butanol
D) 3-methyl-1-butanol
36 Which of the following aldehydes, used solitary, volition undergo an aldol reaction?
A) formaldehyde, CH2O
B) butanal, CH3(CHii)2CHO
C) benzaldehyde, C6H5CHO
D) 2-propenal, CH2=CHCHO
37 Which of the post-obit reaction sequences would be best for preparing 2,ii-dimethyl-3-hexanone from butanal?
A) (i) addition of tert-butylmagnesium bromide in ether; (ii) hydrolysis workup; (three) PCC in CH2Cl2
B) (i) NaBH4; (ii) PBr3; (three) Mg in ether; (iv) 2,ii-dimethylpropanal, followed past hydrolysis
C) (i) Wittig reaction with (CviHfive)iiiP=C(CHiii)2; (ii) BH3 in THF; (three) H2O2 & base; (4) PCC in CHtwoCl2
D) (i) Wittig reaction with (CviHfive)3P=CHC(CHthree)3; (2) BH3 in THF; (three) H2O2 & base of operations; (iv) PCC in CHtwoCl2
38 How can 1,one,i,ii,2-pentadeutero-3,3-dimethylpentane, CtwoH5C(CH3)iiCiiDfive, be prepared from 3,iii-dimethyl-2-pentanone?
A) (i) NaOD in D2O (excess); (ii) LiAlD4 in ether; (iii) D2O workup
B) (i) Wolff-Kishner reduction with N2Div in ROD; (two) NaOD in D2O (excess)
C) (i) Zn & DCl in CH3CO2D; (ii) LiAlD4 in ether; (iii) D2O workup
D) (i) NaOD in DtwoO (backlog); (two) HSCH2CH2SH + BF3; (iii) D2 + Raney Ni catalyst
39 Acetaldehyde reacts with (R)-1,ii-propanediol (acid catalyst) to give two isomeric acetals. What is their isomeric human relationship?
A) they are constitutional isomers
B) ii they are diastereomers
C) 3 they are enantiomers
D) they are conformers
xl What is the product of the post-obit reaction?
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41 What product or products are expected from acrid-catalyzed hydrolysis of the following chemical compound?
A) merely the starting material itself (no reaction)
B) benzaldehyde and 2,2-dimethyl-1,3-propanediol
C) benzoic acid and 2,ii-dimethyl-1,3-propanediol
D) two-phenyl-1,3-propanediol and acetone
42 Base induced emptying of 3-chlorocyclohexanone I is much faster than elimination of cyclohexyl chloride II.
What is the major factor accounting for this deviation?
A) the element of group vii in I is less hindered
B) the halogen in I is forced to be axial
C) elimination of I produces a more than stable conjugated double bond
D) I quickly forms an enolate anion, and this immediately eliminates a stable chloride ion
43 Which of the post-obit optically agile compounds will be racemized on treatment with warm alcoholic sodium ethoxide?
| (R)-2,two,6-trimethylcyclohexanone | (R)-2,2,v-trimethylcyclohexanone | (R)-ii-methyl-2-phenylcyclohexanone | (R)-4-methyl-ii-cyclohexen-i-1 |
| I | II | III | IV |
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B) I and 3
C) I and IV
D) all compounds will be racemized
44 A C5H8 hydrocarbon is reacted with BHthree in THF, followed by oxidation with alkaline metal hydrogen peroxide.
Handling of the resulting product with PCC in CHtwoCltwo produces a chiral ketone, formula CfiveH8O.
What hydrocarbon best fits these facts?
A) i-methylcyclobutene
B) methylenecyclobutane
C) vinylcyclopropane
D) cyclopentene
45 Which of the following compounds would non be a possible product from the mixed aldol reaction of acetaldehyde and butanal?
A) iii-hydroxybutanal
B) 2-ethyl-3-hydroxybutanal
C) three-ethyl-two-hydroxyhexanal
D) iii-hydroxyhexanal
46 A CviiH12Oii compound gives a positive Tollens' silvery mirror test and a positive iodoform test.
Which of the following would satisfy these facts?
A) 2-hydroxy-iii,3-dimethylcyclopentanone
B) 2,v-heptanedione
C) ii,2-dimethyl-3-oxopentanal
D) 2,two-dimethyl-iv-oxopentanal
47 The iodoform test for methyl ketones is not widely used anymore.
Which of the following spectroscopic tools is best for providing equivalent information?
A) UV-Visible
B) 1H nmr
C) 13C nmr
D) infrared
48 An aldol condensation is used to prepare i,iii-diphenyl-2-propenone, C6H5CH=CHCOC6Hv.
Which combination of reactants will lead to this product?
A) enolate donor=acetaldehyde; carbonyl acceptor=benzaldehyde
B) enolate donor=phenylacetaldehyde; carbonyl acceptor=phenylacetaldehyde
C) enolate donor=acetophenone; carbonyl acceptor=benzaldehyde
D) enolate donor=propiophenone; carbonyl acceptor=benzaldehyde
49 Which of the post-obit compounds would exist the major product from aldol condensation of half dozen-oxoheptanal?
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50 Which of the post-obit procedures would not be suitable for preparing 3-methyl-1-phenyl-one-butanone, C6HfiveCOCH2CH(CH3)ii?
A) (i) C6H5COCH=CHCH3 + (CHthree)2CuLi in ether; (two) H3O+ workup
B) (i) benzene + (CHiii)2CHCH2COCl & AlCliii (2) HiiiO+ workup
C) (i) C6H5MgBr + (CH3)2CHCH2CHO in ether; (ii) HiiiO+ workup; (iii) PCC in CH2Cl2
D) (i) (CH3)twoCHMgBr + C6H5COCH3 in ether; (ii) H3O+ workup; (iii) PCC in CH2Cl2
51 Formulas for four ethyl ethers are drawn beneath. 2 are broken by aqueous acid much more than easily than the other ii.
Which ethers are more easily hydrolyzed?
A) I and II
B) Two and Three
C) Three and 4
D) I and IV
52 The Wieland-Miescher ketone is an important synthetic intermediate. Its formula is shown below.
What starting materials would be suitable for preparing this compound by a combination of Michael and aldol reactions?
A) four-methyl-2-cyclohexen-1-one and 3-butenal
B) two-methylcyclohexane-1,iii-dione and three-buten-2-i
C) 2-methyl-2-vinyl-3-cyclohexen-one-1 and acetaldehyde
D) ii-methyl-2-cyclohexen-ane-one and ane,four-dichlorobutan-2-ane
53 2,2-Dimethyl-ane,3-propanediol is coveniently prepared by heating 2-methylpropanal with backlog formaldehyde and Ca(OH)two.
What sequence of reactions takes place in this synthesis?
A) dehydrogenation to two-methyl-2-propenal followed by improver of formaldehyde
B) dehydrogenation to dimethylketene followed past addition of formaldehyde
C) a crossed aldol reaction followed by a crossed Cannizzaro reaction
D) a crossed Cannizzaro reaction followed past a crossed aldol reaction
54 A bis-aldol dimerization of one-phenyl-one,two-propanedione, Chalf-dozenH5COCOCH3, gives which of the post-obit?
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55 What donor and acceptor reactants should be used to prepare the post-obit compound past an aldol reaction?
A) acceptor = formaldehyde; donor = propanedial
B) acceptor = 1,iii-propanediol; donor = ethanal
C) acceptor = propanal; donor = formaldehyde
D) acceptor = formaldehyde; donor = propanal
56 What donor and acceptor reactants should be used to ready the following compound by an aldol condensation (or Claisen-Schmidt reaction)?
A) acceptor = cyclopentanone; donor = benzaldehyde
B) acceptor = benzaldehyde; donor = cyclopentanone
C) acceptor = phenylacetaldehyde; donor = cyclopentanone
D) acceptor = cyclopentanecarbaldehyde; donor = toluene
57 The formula of brevicomin, a pheremone of the western pine beetle, is shown below.
What open concatenation ketodiol would close to this bicyclic acetal? (ignore stereoisomer issues)
A) seven,8-dihydroxynonan-3-one
B) 6,7-dihydroxynonan-3-one
C) 7,viii-dihydroxynonan-2-one
D) 6,7-dihydroxynonan-two-one
58 The formula of multistriatin, a pheremone of the elm bark beetle, is shown below.
What open chain ketodiol would close to this bicyclic acetal? (ignore stereoisomer issues)
A) 3-ethyl-5-methyl-half-dozen,7-dihydroxyheptan-2-1
B) 4,6-dimethyl-7,8-dihydroxyoctan-3-1
C) four-methyl-7,eight-dihydroxynonan-iii-one
D) 3-ethyl-half-dozen,7-dihydroxyoctan-two-1
59 A conversion of 2,5-dimethylfuran into ii,v-dimethylpyrrole (see equation) may exist accomplished in two steps.
i) hydrolysis of the furan in aqueous acrid; ii) heating the hydrolysis product with excess ammonium carbonate
What is the intermediate hydrolysis product used in the second step?
A) 2,5-hexanedione
B) 3,iv-hexanedione
C) hexanedial
D) 2,five-dimethylcyclopentanone
threescore The reagent semicarbazide, NH2CONHNH2, reacts with simple aldehydes and ketones (RtwoC=O) forming crystalline derivatives called semicarbazones.
Which of the post-obit represents the structure of a semicarbazone?
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61 Which of the post-obit compounds (I through 5) should not be classified as an acetal?
A) II & III
B) IV
C) I
D) none (they are all acetals)
Source: https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/questions/problems/exam8.htm
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