Reviewquestions_18

Reviewquestions_18 - 1) Which of the following correctly...

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1) Which of the following correctly describes the bond angle and hybridizations present in formaldehyde? A) C, sp 2 ; O, sp 3 ; HCO, ~120° B) C, sp 2 ; O, sp 2 ; HCO, ~120° C) C, sp 2 ; O, sp 2 ; HCO, ~109.5° D) C, sp 3 ; O, sp 2 ; HCO, ~109.5° E) C, sp 3 ; O, sp 3 ; HCO, ~109.5° Answer: B Diff: 1 2) Would you expect the carbonyl carbon of benzaldehyde to be more or less electrophilic than that of acetaldehyde? Explain using resonance structures. Answer: The carbonyl carbon of benzaldehyde would be less electrophilic. Delocalization reduces its partial positive charge as seen in the resonance forms below. Diff: 2 3) Provide the proper IUPAC name for (CH 3 ) 2 CHCH 2 CH 2 COCH=CH 2 . Answer: 6-methylhept-1-en-3-one Diff: 2 4) Provide the proper IUPAC name for PhCH 2 CH(CH 3 )CH 2 CH 2 CHO. Answer: 4-methyl-5-phenylpentanal Diff: 1 5) Provide the proper IUPAC name for CH 3 CHOHCH 2 COCH 2 C(CH 3 ) 2 CH 2 CH 3 . Answer: 2-hydroxy-6,6-dimethyl-4-octanone Diff: 1 8) Provide the structure of benzophenone. Answer: PhCOPh Diff: 1 1
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9) Provide the structure of cyclohexanone oxime. Answer: Diff: 2 10) Provide the structure of the diethyl acetal of butanal. Answer: CH 3 CH 2 CH 2 CH(OCH 2 CH 3 ) 2 Diff: 2 13) Provide the structure of the semicarbazone derivative of 3-pentanone. Answer: Diff: 3 2
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16) How might one distinguish an aldehyde from a ketone using IR data alone? Answer: The aldehyde has two C-H stretches at 2700 and 2800 cm -1 . Diff: 2 17) When a carbonyl is part of a conjugated π -network, the C=O stretch: A) has a higher frequency than in a nonconjugated system. B) has a lower frequency than in a nonconjugated system. C) always occurs at 1710 cm -1 . D) occurs around 2700 cm -1 . E) cannot be distinguished from the C=O stretch in a nonconjugated system. Answer: B Diff: 2 20) The proton NMR spectrum of an unknown compound contains a triplet at 9.8 ppm. Which of the following could be this unknown? A) (CH 3 ) 3 CCHO B) CH 3 CH 2 CH 2 CO 2 H C) CH 3 CH 2 CH 2 CHO D) CH 3 CO CH 2 Ph E) PhCHO Answer: C Diff: 2 21) Provide the major organic product which results when PhCHO is treated with the following sequence of reagents: 1. CH 3 CH 2 MgBr; 2. H 3 O+; 3. Na 2 Cr 2 O7, H 2 SO 4 . Answer: PhCOCH 2 CH 3 Diff: 1 22) By which single reaction can benzene be readily converted into acetophenone? Answer: CH 3 COCl, AlCl 3 - a Friedel-Crafts acylation reaction Diff: 2 3
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23) What reagents can be used to convert 1-hexyne into 2-hexanone? A) 1. Sia 2 BH; 2. H 2 O 2 , NaOH B) Hg 2+ , H 2 SO 4 , H 2 O C) 1. O 3 ; 2. (CH 3 ) 2 S D) 1. CH 3 MgBr; 2. CO 2 E) 1. H 2 , Ni; 2. Na 2 Cr 2 O 7 , H 2 SO 4 Answer: B Diff: 2 24) What reagent can be used to convert benzophenone into triphenylmethanol? Answer: PhMgBr followed by acidic work up
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This note was uploaded on 03/18/2010 for the course DSAG asdg taught by Professor Asdg during the Spring '10 term at 東京国際大学.

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Reviewquestions_18 - 1) Which of the following correctly...

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