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 fom hydRogen bonds with WateR and is moRe soLube than C3C2C2CH2CH3 which cannot Form hydRogen bonds with wate (b) CH3CH2NHCH3 is MoRe ater soube becAuse it can fom hydrogen bonds; CH3CH2CH2CH3 cannot foRm hydRogen bonds (c) CH3CH2 H is moRe soLuBe in wateR. The poLAR OH gRoup Foms hydRogen bonds With wAteR, oVeRcong the Resistance of the nonpoLaR CH3CH2 gRoup toaRd enteing the waeR n CH3CH2CH2CH2 H hoWeVeR, the hydRogen bonding FRom ony one OH gRoup cannot cay a fouRcaRbon can nto the ateR this substAnce is onLy sLightLy soLubLe in WateR (d) oth compounds Fo hydRogen bonds With water At the doubebonded oxygen, but ony he smaeR MoLecuLe (CHCOCH dissoVes The cycc copound hAs too MAny nonpoLaR CH gRoups to dissoLe. 32...
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