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### Aldehydes and Ketones

1.

You are watching: Which of the following reactions can be used to prepare 3-methyl-3-hexanol,

which of the adhering to is a correct surname for (CH3)2C=CHCOCH3? A) 2-methyl-2-penten-4-one B) 4-methyl-3-penten-2-one C) 1,3-dimethyl-2-pentenal D) isopentenone

2. i m sorry of the adhering to is 3,3-diphenylpropanal? A) C6H5CH2CH(C6H5)CHO B) C6H5CH2CH2COC6H5 C) (C6H5)2CHCH2CHO D) (C6H5)2CHCH2COC6H5

3. which of the following compounds is not named correctly?
 A) 2-methyl-3-heptanone (CH3)2CHCOCH2CH2CH2CH3 B) phenylacetaldehyde C6H5CH2CHO C) 4-hexyn-2-one CH3COCH2C≡CCH3 D) para-bromoacetophenone p-BrC6H4CH2COCH3

4. i beg your pardon of the complying with compounds is not called correctly?

5. i m sorry of the adhering to compounds is not called correctly?

6 Which the the adhering to may it is in classified as an acetal? A) ns & II B) III & IV C) only IV D) all yet IV

7Which of the following reactions is a great method because that preparing one aldehyde? A) Jones" reagent and a 1º-alcohol B) Jones" reagent and a 2º-alcohol C) PCC and a 1º-alcohol D) H2SO4 a 1º-alcohol and also heat

8Which of the complying with are enol tautomers that 3-methylcyclohexanone? A) ns & II B) i & IV C) II & III D) just I

9Which the the adhering to statements is not generally true? A) C=O is stronger than an indistinguishable C=C B) C=O has actually a bigger bond dipole than C=C C) aldehydes and ketones have greater boiling point out than similarly sized alkenes D) alkenes include nucleophiles an ext rapidly 보다 aldehydes or ketones of comparable structure

10Which of the adhering to compounds exchanges the largest number of hydrogens because that deuterium as soon as treated v KOD in D2O? A) 3-methyl-1,2-cycloheptanedione B) 2-methyl-1,3-cycloheptanedione C) 5-methyl-1,3-cycloheptanedione D) 6-methyl-1,4-cycloheptanedione

11Four C8H14O ketones are examined through 13Cnmr spectroscopy. one of them has five unique carbon signals. Which of the complying with fits this fact? A) 4,4-dimethylcyclohexanone B) 3,3-dimethylcyclohexanone C) 2,2-dimethylcyclohexanone D) 2,2,4,4-tetramethylcyclobutanone

12Which of the adhering to compounds could not be converted to pentanal in one or two steps? A) 1-pentyne B) trans-5-decene C) 2-pentanone D) 1-pentanol

13Treatment the cyclohexanone through an overabundance of H218O produce 18O labeled cyclohexanone. i beg your pardon of the following is a most likely intermediate in this isotope exchange? (the isotope is not named) A) 1-cyclohexen-1-ol B) 1,1-cyclohexanediol C) 2-cyclohexen-1-one D) 1,2-cyclohexanediol

14Reaction that C6H5CHBr2 with NaOH in aqueous THF is likely to develop which product? A) C6H5CHBrOH B) C6H5CH(OH)2 C) C6H5CHO D) C6H5CO2H

15Which the the following carbonyl compound reacts most rapidly v nucleophilic reagents? A) benzaldehyde B) 3,3-dimethylbutanal C) acetophenone D) 2,2-dimethylcyclohexanone

16Which that the adhering to amines would be best chosen for preparing one enamine derivative indigenous cyclohexanone? A) dimethylamine B) ethylamine C) trimethylamine D) hydroxylamine

17Which reaction or sequence of reactions would certainly best accomplish the following synthesis? A) CH3NH2, acid catalyst & heat B) CH2=NH, acid catalyst & warmth C) (i) NH3 acid catalyst & heat; (ii) CH2I2 & Zn(Cu) D) (i) HCN & NaCN; (ii) LiAlH4 in ether

18Heating cyclopentanone v either: I ethyl amine, or II diethylamine, together with an acid catalyst leads to various results. i beg your pardon of the following ideal describes this difference? A) I offers an imine & II fails to react B) I gives an enamine & II falls short to reaction C) I offers an imine & II provides an enamine D) I gives an enamine & II offers an imine

19Which reaction or sequence of reactions would be best used to transform cyclohexanone to cis-1,2-cyclohexanediol? A) PCC in CH2Cl2 and also base B) (i) NaBH4; (ii) H3PO4 & heat; (iii) OsO4 in pyridine C) (i) NaBH4; (ii) H3PO4 & heat; (iii) C6H5CO3H D) (i) NaBH4; (ii) OsO4 in pyridine

20A C9H10O compound has a solid absorption in ~ 1686 -1cm in the infrared. which of the complying with compounds would certainly be expected to screen such an absorb band?

21A C9H10O compound has actually a solid absorption in ~ 1730 and two smaller but sharp absorb peaks at 2719 & 2818 -1cm in the infrared. The 1Hnmr has a solid doublet in ~ δ1.0 ppm. which of the complying with compounds would be meant to display screen these features?

22The Wittig reaction takes place between a carbonyl compound and a phosphorus ylid. i m sorry of the adhering to represents the dipolar contributor to together an ylide? A) ns & II B) II just C) III just D) i & IV

23Which that the complying with reaction sequences would certainly be ideal for convert cyclohexanol to methylenecyclohexane, (CH2)5C=CH2 ? A) (i) H3PO4 & heat; (ii) CH2I2 + Zn(Cu) B) (i) PCC in CH2Cl2; (ii) CH3MgBr; (iii) H3PO4 & heat C) PCC in CH2Cl2; (ii) (C6H5)3P=CH2 D) CH2N2 & warm

24Which of the adhering to Wittig reagents would be useful for converting R2C=O right into R2CHCH=O? A) (C6H5)3P=CH-OCH3 B) (C6H5)3P=CH-CH3 C) (C6H5)3P=Cl2 D) (C6H5)3P=CH-CH=CH2

25Two equivalents that the Wittig reagent (CH3)2C=CH-CH=P(C6H5)3 were enabled to react v a C4H4O2 compound. The chief product was 2,11-dimethyl-2,4,6,8,10-dodecapentaene, (CH3)2C=CH(CH=CH)3CH=C(CH3)2. What was the C4H4O2 compound offered in this reaction? A) 2-butyne-1,4-diol B) 1,2-cyclobutanedione C) 1,3-butadien-2,3-diol D) 2-butenedial

26Which the the adhering to reactions would not it is in a useful method of preparing 1-phenyl-2-butanol? A) phenylacetaldehyde + ethylmagnesium bromide B) butanal + phenylmagnesium bromine C) propanal + benzylmagnesium bromine D) 1-phenyl-2-butanone + NaBH4

27Which that the complying with reactions would not it is in a useful method of preparing 2-phenyl-2-butanol? A) 2-butanone + phenylmagnesium bromine B) acetophenone + ethylmagnesium bromide C) cis-2,3-dimethyloxirane + phenylmagnesium bromide D) ethylphenylketone + methylmagnesium iodide

28In the reaction of (R)-3-phenyl-2-butanone v methylmagnesium iodide, what happens to the configuration of the stereogenic center? A) nothing, it remains unchanged B) inversion takes location C) racemization occurs D) the product is achiral

29Which the the adhering to reactions would not be helpful for converting 4,4-diethylcyclohexanone into 1,1-diethylcyclohexane? A) Wolff-Kishner palliation (N2H4, strong base & heat) B) Clemmensen reduction (Zn/Hg, mountain & heat) C) thioacetal palliation (i HSCH2CH2SH & BF3; ii H2 + Raney Ni) D) LiAlH4 in THF & heat

30Which the the adhering to is a semicarbazone derivative of an aldehyde (RCHO)? A) RCH=N-NHCONH2 B) RCH=N-OH C) RCH=N-NH2 D) RCH=N-C(CH3)3

31Which the the complying with isomers is most acidic ? A) 3,4-hexanedione B) 2,5-hexanedione C) 2,4-hexanedione D) hexanedial

32You have actually two C6H10O ketones, I and also II. Both room optically active, yet I is racemized by treatment with base and also II is not. Wolff-Kishner reduction of both ketones provides the very same achiral hydrocarbon, formula C6H12. What reasonable structures may be assigned to I and II? A) I is 3-methyl-4-penten-2-one; II is 4-methyl-1-penten-3-one B) I is 2-methylcyclopentanone; II is 3-methylcyclopentanone C) I is 3-methylcyclopentanone; II is 2-methylcyclopentanone D) I is 2-ethylcyclobutanone; II is 3-ethylcyclobutanone

33Jones" reagent oxidizes aldehydes come carboxylic acids yet normally does not oxidize ketones. What intermediate types is most most likely responsible for the aldehyde oxidation? A) a carbonyl hydrate B) an enol tautomer C) one oxonium conjugate mountain of the aldehyde D) an acylium cation34The lithium enolate base from cyclohexanone reacts with alkyl halides, frequently in different ways. As presented here, methyl iodide and tert-butyl bromide reaction to give different organic products, I and II, together with lithium halides. What room the commodities from this reactions? A) I is 2-methylcyclohexanone; II is 2-t-butylcyclohexanone B) I is 1-methoxycyclohexene; II is 1-t-butoxycyclohexene C) I is 2-methylcyclohexanone; II is 1-t-butoxycyclohexene D) I is 2-methylcyclohexanone; II is a mixture that cyclohexanone and also 2-methylpropene

35A C5H12O link is optically active, and also is oxidized by PCC in CH2Cl2 to an optically active C5H1OO product, i beg your pardon is racemized in acid or base. which of the following finest fits these facts? A) 2-pentanol B) 2-methoxybutane C) 2-methyl-1-butanol D) 3-methyl-1-butanol

36Which that the following aldehydes, used alone, will undergo one aldol reaction? A) formaldehyde, CH2O B) butanal, CH3(CH2)2CHO C) benzaldehyde, C6H5CHO D) 2-propenal, CH2=CHCHO

37Which of the following reaction sequences would certainly be finest for prepare 2,2-dimethyl-3-hexanone from butanal? A) (i) enhancement of tert-butylmagnesium bromide in ether; (ii) hydrolysis workup; (iii) PCC in CH2Cl2 B) (i) NaBH4; (ii) PBr3; (iii) Mg in ether; (iv) 2,2-dimethylpropanal, adhered to by hydrolysis C) (i) Wittig reaction through (C6H5)3P=C(CH3)2; (ii) BH3 in THF; (iii) H2O2 & base; (iv) PCC in CH2Cl2 D) (i) Wittig reaction v (C6H5)3P=CHC(CH3)3; (ii) BH3 in THF; (iii) H2O2 & base; (iv) PCC in CH2Cl2

38How deserve to 1,1,1,2,2-pentadeutero-3,3-dimethylpentane, C2H5C(CH3)2C2D5, be prepared from 3,3-dimethyl-2-pentanone? A) (i) NaOD in D2O (excess); (ii) LiAlD4 in ether; (iii) D2O workup B) (i) Wolff-Kishner reduction through N2D4 in ROD; (ii) NaOD in D2O (excess) C) (i) Zn & DCl in CH3CO2D; (ii) LiAlD4 in ether; (iii) D2O workup D) (i) NaOD in D2O (excess); (ii) HSCH2CH2SH + BF3; (iii) D2 + Raney Ni catalyst

39Acetaldehyde reacts with (R)-1,2-propanediol (acid catalyst) to give two isomeric acetals. What is their isomeric relationship? A) they space constitutional isomers B) 2 they are diastereomers C) 3 they are enantiomers D) they are conformers

40What is the product that the following reaction?

41What product or commodities are supposed from acid-catalyzed hydrolysis that the complying with compound? A) just the starting material itself (no reaction) B) benzaldehyde and 2,2-dimethyl-1,3-propanediol C) benzoic acid and 2,2-dimethyl-1,3-propanediol D) 2-phenyl-1,3-propanediol and acetone

42Base induced elimination of 3-chlorocyclohexanone I is much much faster than removed of cyclohexyl chloride II. What is the major factor audit for this difference? A) the halogen in I is much less hindered B) the halogen in I is required to it is in axial C) remove of I to produce a much more stable conjugated dual bond D) I rapidly forms an enolate anion, and this instantly eliminates a stable chloride ion

43Which of the adhering to optically energetic compounds will be racemized on treatment with warm alcoholic sodium ethoxide? IIIIIIIV
 (R)-2,2,6-trimethylcyclohexanone (R)-2,2,5-trimethylcyclohexanone (R)-2-methyl-2-phenylcyclohexanone (R)-4-methyl-2-cyclohexen-1-one
A) I
and II B) I and also III C) I and also IV D) every compounds will certainly be racemized

44A C5H8 hydrocarbon is reacted with BH3 in THF, complied with by oxidation through alkaline hydrogen peroxide. therapy of the resulting product v PCC in CH2Cl2 produces a chiral ketone, formula C5H8O. What hydrocarbon ideal fits these facts? A) 1-methylcyclobutene B) methylenecyclobutane C) vinylcyclopropane D) cyclopentene

45Which of the adhering to compounds would not it is in a possible product native the blended aldol reaction of acetaldehyde and butanal? A) 3-hydroxybutanal B) 2-ethyl-3-hydroxybutanal C) 3-ethyl-2-hydroxyhexanal D) 3-hydroxyhexanal

46A C7H12O2 compound offers a positive Tollens" silver mirror test and a positive iodoform test. i m sorry of the adhering to would satisfy these facts? A) 2-hydroxy-3,3-dimethylcyclopentanone B) 2,5-heptanedione C) 2,2-dimethyl-3-oxopentanal D) 2,2-dimethyl-4-oxopentanal

47The iodoform test because that methyl ketones is not widely supplied anymore. which of the complying with spectroscopic devices is ideal for providing equivalent information? A) UV-Visible B) 1H nmr C) 13C nmr D) infrared

48An aldol condensation is offered to prepare 1,3-diphenyl-2-propenone, C6H5CH=CHCOC6H5. Which mix of reaction will cause 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

49Which of the adhering to compounds would be the major product indigenous aldol condensation the 6-oxoheptanal?

50Which the the following procedures would not be perfect for preparing 3-methyl-1-phenyl-1-butanone, C6H5COCH2CH(CH3)2? A) (i) C6H5COCH=CHCH3 + (CH3)2CuLi in ether; (ii) H3O+ workup B) (i) benzene + (CH3)2CHCH2COCl & AlCl3 (ii) H3O+ workup C) (i) C6H5MgBr + (CH3)2CHCH2CHO in ether; (ii) H3O+ workup; (iii) PCC in CH2Cl2 D) (i) (CH3)2CHMgBr + C6H5COCH3 in ether; (ii) H3O+ workup; (iii) PCC in CH2Cl2

51Formulas for 4 ethyl ethers are attracted below. Two space cleaved by aqueous mountain much more easily than the other two. which ethers are more easily hydrolyzed? A) I and also II B) II and III C) III and also IV D) I and IV

52The Wieland-Miescher ketone is an important synthetic intermediate. That formula is displayed below. What starting materials would be suitable for prepare this compound by a mix of Michael and aldol reactions? A) 4-methyl-2-cyclohexen-1-one and 3-butenal B) 2-methylcyclohexane-1,3-dione and also 3-buten-2-one C) 2-methyl-2-vinyl-3-cyclohexen-1-one and also acetaldehyde D) 2-methyl-2-cyclohexen-1-one and also 1,4-dichlorobutan-2-one

532,2-Dimethyl-1,3-propanediol is coveniently prepared by heating 2-methylpropanal v excess formaldehyde and Ca(OH)2. What sequence of reactions takes ar in this synthesis? A) dehydrogenation come 2-methyl-2-propenal adhered to by enhancement of formaldehyde B) dehydrogenation to dimethylketene adhered to by enhancement of formaldehyde C) a overcome aldol reaction adhered to by a overcome Cannizzaro reaction D) a crossed Cannizzaro reaction adhered to by a crossed aldol reaction

54A bis-aldol dimerization the 1-phenyl-1,2-propanedione, C6H5COCOCH3, gives which that the following?

55What donor and also acceptor reactants should be supplied to prepare the following compound by an aldol reaction? A) acceptor = formaldehyde; donor = propanedial B) acceptor = 1,3-propanediol; donor = ethanal C) acceptor = propanal; donor = formaldehyde D) acceptor = formaldehyde; donor = propanal

56What donor and acceptor reactants need to be used to prepare 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

57The formula the brevicomin, a pheremone that the west pine beetle, is presented below. What open up chain ketodiol would certainly close come this bicyclic acetal? (ignore stereoisomer issues) A) 7,8-dihydroxynonan-3-one B) 6,7-dihydroxynonan-3-one C) 7,8-dihydroxynonan-2-one D) 6,7-dihydroxynonan-2-one

58The formula that multistriatin, a pheremone the the elm bark beetle, is presented below. What open chain ketodiol would close to this bicyclic acetal? (ignore stereoisomer issues) A) 3-ethyl-5-methyl-6,7-dihydroxyheptan-2-one B) 4,6-dimethyl-7,8-dihydroxyoctan-3-one C) 4-methyl-7,8-dihydroxynonan-3-one D) 3-ethyl-6,7-dihydroxyoctan-2-one

59A conversion of 2,5-dimethylfuran into 2,5-dimethylpyrrole (see equation) might be completed in two steps.

See more: Newto N/M To Dyne/Cm - Convert Newton Meters To Dyne Centimeters

i) hydrolysis the the furan in aqueous acid; ii) heater the hydrolysis product v excess ammonium lead carbonate What is the intermediary hydrolysis product supplied in the second step? A) 2,5-hexanedione B) 3,4-hexanedione C) hexanedial D) 2,5-dimethylcyclopentanone

60The reagent semicarbazide, NH2CONHNH2, reacts with straightforward aldehydes and ketones (R2C=O) developing crystalline derivatives called semicarbazones. which of the adhering to represents the framework of a semicarbazone?

61Which of the complying with compounds (I with V) must not be classified together an acetal? A) II & III B) IV C) i D) nobody (they space all acetals)