16_all_ - 16-1.(a)Give IUPAC substitutive names for the...

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16-1.(a)Give IUPAC substitutive names for the seven isomeric aldehydes and ketones with the formula C 5 H 8 O (b).Give structures and names (common or IUPAC substitutive names)for all the aldehydes and ketones that contain a benzene ring and have the formula C 8 H 8 O An: (a) H O pentanal H O 3-methyl butanal H O 2-methyl butanal H O 2,2-dimethyl propanal O 2-pentanone O 3-pentanone O 4-methyl butanone (b) H O phenylacetaldehyde O acetophenone
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H O 2-methylbenzaldehyde H O 3-methyl benzaldehyde O H 4-methyl benzaldehyde 16-2.Which compound in each of the following pairs listed has the higher boiling point? (Answer this problem without consulting tables.) (a) Pentanal or 1-pentanol An: 1-pentanol (H bonds) (b) 2-Pentanone or 2-pentanol An: 2-pentanol (H bonds) (c) Pentane or pentanal An: pentanal (more polarized) (d) Acetophenone or 2-phenylethanol An: 2-phenylethanol (H bonds) (e) Benzaldehyde or benzyl alcohol An: benzyl alcohol (H bonds) 16.3 Show how you would synthesize propanal from each of the following: (a) 1-propanol
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CH 3 CH 2 CH 2 OH + CH 3 2 CHO PCC (b) propanoic acid (CH 3 CH 2 CO 2 H) CH 3 CH 2 COH O SOCl 2 CH 3 CCl O (1)LiAlH(o-t-Bu) 3 -78 (2)H 2 O CH 3 CH 2 O 16.4 (a) Benzene bromobenzene phenylmagnesium bromide benzyl alcohol benzaldehyde Br 2 Br Mg Et 2 O 35 MgBr (1)HCHO (2)H 2 O CH 2 OH C O H PCC (b) Toluene benzoic acid benzoyl chloride benzaldehyde CH 3 KMnO 4 H + C O OH COCl C O H SOCl 2 LiAlH[OC(CH 3 ) 3 (c) Ethyl bromide 1-butyne butanone CH 3 CH 2 Br + Hg 2 + / H 2 O O (d) 2-Butyne butanone C CCH 3 H 3 C HgSO 4 H 2 SO 4 O H 3 C CH 2 CH 3 (e) 1-phenylethanol acetophenone CH 3 OH H 2 CrO 4 C 3 O (f) Benzene acetophenone + O H 3 C Cl CH 3 O AlCl 3 (g) Benzoyl cholride acetophenone
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Cl O (CH 3 ) 2 CuLi CH 3 O (h) Benzoic acid acetophenone C O OH SOCl 2 Cl O (CH 3 ) 2 CuLi CH 3 O (i) Benzyl bromide C 6 H 5 CH 2 CN 1-phenyl-2-butanone CH 2 Br NaCN CH 2 CN 3 CH 2 MgBr + Et 2 O H 3 + O O (j) C 6 H 5 CH 2 CN 2-phenylethanal 2 CN (1)H-Al(i-Bu) 2 (2)H 2 O O H (k) CH 3 (CH 2 ) 4 CO 2 CH 3 hexanal C O OCH 3 H 3 C(H 2 C) 4 (1)DIBAL-H hexane -78 (2)H 2 O H 3 C(H 2 4 C O H 16.5 The reaction of an aldehyde or ketone with a Grignard reagent (Section 12.8) is a nucleophilic addition to the carbon-oxygen double bond. (a) What is the nucleophile? (b) The magnesium portion of the Grignard reagent plays an important part in this reaction. What is its function? (c) What product is formed initially? (d) What product forms when water is added? Answer: (a) R¯ in RMgX is the nucleophile. (b) Making the polarity of the carbon reversed (c) BrMgO R R R (d) HO R R R 16.6 The reactions of aldehydes and ketones with LiAlH4 and NaBH4 (Section 12.3) are nucleophilic additions to the carbonyl group . What is the nucleophile in these reactions?
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Answer: H¯ 16.7 Dissolving formaldehyde in water leads to a solution containing primarily the gemdiol, CH 2 (OH) 2 Show the steps in its formation from formaldehyde.
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This note was uploaded on 02/23/2010 for the course CHEM 101 taught by Professor Smith during the Spring '10 term at Duke.

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16_all_ - 16-1.(a)Give IUPAC substitutive names for the...

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