Solutions_Manual_for_Organic_Chemistry_6th_Ed 42

Solutions_Manual_for_Organic_Chemistry_6th_Ed 42 - (a...

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(hydrogen bonds shown as wavy bond) 2-17 (a) (CH3±CHCH2CH2CH(CH3± has less brAnching And boiLs at A higheR tempeRature than (CH3²CC(CH3² . (b) CH3(CH2³SCH2 0 H can fo´m hydRogen bonds And WiLL boiL at a much higheR tempeRatuRe than CH3(CH2³6Cµ3 which cAnnot fo´m hydRogen bonds¶ (c) HOCH2(CH2³4CH2 0 H can Fo·m hydrogen bonds At both ends and has no BRanching; it wiLL boiL at A Much higheR teMperatuRe than (CH3²CCH¸OH³CH3 . ¹d) (CH3CH2CH2±NH hAs an º-H bond And can Fo´m hydRogen Bonds; it wiL» boiL at a hIgheR te¼peRature t½an (CH3CH2²N which cAnnot fo·m hydRogen bonds¶ (e) The second compound shown (B) hAs the higher boiLing point for t¾o Reasons: B has a hIgheR MoLecuLaR ¾eight thAn A; And B, a pr¿MARy AmIne ¾ith t¾o º-À bonds, has more oppo·tunity FoR Forming hydRogen bonds than A,
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Unformatted text preview: (a) CH3CH2 CH2CH3 can fo´m hydRogen bonds with WateR and is moRe soLub»e than Cµ3CÀ2CÀ2CH2CH3 which cannot Form hydRogen bonds with wate´Â (b) CH3CH2NHCH3 is MoRe ¾ater soÃubÃe becAuse it can fo·m hydrogen bonds; CH3CH2CH2CH3 cannot foRm hydRogen bonds¶ (c) CH3CH2 H is moRe soLuB»e in wateR. The poLAR OÄH gRoup Fo·ms hydRogen bonds With wAteR, oVeRcoÅng the Resistance of the nonÆpoLaR CH3CH2 gRoup to¾aRd ente´ing the waÇeRÈ Én CH3CH2CH2CH2 HÊ hoWeVeR, the hydRogen bonding FRom on»y one OH gRoup cannot caËy a fouRÌcaRbon cÍaÎn Ïnto the ¾ateRÐ this substAnce is onLy sLightLy soLubLe in WateRÑ (d) Ò oth compounds FoÓ hydRogen bonds With water At the doub»eÔbonded oxygen, but onÕy Öhe sma»»eR MoLecuLe (CH×COCH׳ dissoÃVesØ The cycÃÙc coÚpound hAs too MAny nonÆpoLaR CHÛ gRoups to dissoLÜe. 32...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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