Chemical Structures, Nomenclature, and Resonance for Organic Compounds - Prof. Geoffrey Mi, Exams of Organic Chemistry

Download Chemical Structures, Nomenclature, and Resonance for Organic Compounds - Prof. Geoffrey Mi and more Exams Organic Chemistry in PDF only on Docsity! 1. (8 points) Provide the chemical structures for the following compounds: a) trans-1,4-diethylcycloheptane r .....).,~,,'1I, •.U'1"""1 ~.Zl'€);, .\ # <D \ Ie t,~"h. <D ,j It~ I LD r (>" ••• ~'o,.~") b) 1-sec-butyl-2-methylcyclohexane r.',.') S""L~ CD Jt (j) ~e( - c.., ",~t,.,(i) \'~\. 'J 2. (8 points) Provide names for the following compounds: Ci .4<w~ l' (Jy1e}. ~ 1iP1~ 45 ", /J" ..,. W;Nt., #t',..r t·'S .,. -II"'I>I'IS vo6o a} 1; b} .• 'I'~7 F F (I~~4 1-1 ~-J.'{/4oJ'~ ~r>111""., ) -l+- W fill') (j) 4!,h, o,Jf!, I-t-;'.,).~ (£) 3. (12 points) Draw all of the possible structural isomers for C7H14 that would be named as a cyclopentane, cyclohexane, or cycloheptane by the IUPAC system. <5 ,\ I, ), q-:s"1r ••1.,I,,,-tfl'W EJ) ;)- "",•.'\1•.,,- +-k -'''0'''/ t1( t..,,,e. 4. (6 points) For the structure below: 2 a) Circle all the methine groups. b) How many of the following types of carbon are present in the molecule? primary (1°):.-S- secondary (2°):..:1... tertiary (3°):_(_ quaternary (40):_'_ ., ~. (6 points) For the compound below, indicate how many carbons have the following hybridization: sp z.. OH b) 6. (14 points) Show all reasonable resonance structures for the following species. For cr indicate which resonance structure you feel is the major contributor and explain why. ( r" /' I" C:::;) , E1 tev·..•.•4 I a) N03- <lei :? (u"'~J/ ~/J .. ~ !'J t •• ~ efc. ~ ~:'R/~~~~ "c:1v't~b (]( ~j) I,l. ('",~f.~ ~M f I I I f 4,."._ .•.• , ...• q II" It' CS-~7T ('U l ') ~ dOel' o...,:s ';(h«.(""') ~~. (,flter N~ ~ 2.. Y"'>;r ~ 0•• (P:f &0t0'00e,. b I( tt::> 0., () tv -, ~O(t{.s fb~ft - O( t'e'(os {h-" (@fe ---:> J~.,f ~II en.l} r·o•~ __ O'(tt -:;;- E):) J c) ~O:CH ~(f)1V 3 c-