Houston Community CollegeSystemOrganic Chemistry II2425SampleEXAM # 2A(16,17, and 18)Cholesterol- is a lipid found in the cell membranes of all animal tissues, and it istransported in the blood plasma of all animals. 1CHE 2425 !ample E"# $ 2# % Chapters &'-&() *irections- +lease ,rite your correct ans,er ne-t to each .uestion number in space pro/ided._____1. Which of the following would you expect to have the highest boiling point? A. isopropyl alcohol B. t-butyl alcoholC. diethyl ether . n-butanol_____!. Which of the following would be the highly "iscible with #$"ost soluble in% water? A. C&'- C&! ( C&! ( C&!)& B. C&' ( C)&% ( C&!- C&' C.C&' ( C#C&'%! ( C&!)&. C&' ( C#C&'%! #)&%_____'. What reagents are typically re*uired to acco"plish allylic bro"ination of an al+ene?A. Br!,&Br B. -B./C&!Cl!C. Br!,CCl0 . Br!,1eBr'_____0. Which of the following are only "eta directing strongly deactivating group#s%?2. (C&'22.(C&)222.()& 23.( -)! A.2 and 23B. 22 and 23 C. 24 224 and 222. only 23_____5. What is the product of refluxing "ethylethyl ether with &2 in acidic solution? A. ethanol and "ethyl iodide B. "ethanol and ethyl iodide C. ethanol and "ethyl alcohol . iodoethane and "ethanol_____ 6. Which of the following is the electrophile that attac+s the aro"atic ring during nitration? A. -)! B. &-)', C. -)'( . -)!,_____7. Which of the following functional group represents the ben8yl group? A. C6&5) ( B. C6&5 ( C. C6&5C&! ( . C6&11C&!( _____9.Which of the following is #bro"o"ethyl%ethyl ether?A.C&'C&! ( ) ( C&!BrB. C&' ( ) (C&!Br C.C&' ( ) - C&!-C&!- Br . C&'C&! ( )- C&!C&!Br!_____:.!-;ethoxypentane is classified as ______________________ .A. a sy""etrical etherB.a secondary alcoholC.an epoxide. an ether_____1-C&)>- C&!)&A.an oxidationB. a reduction C.hydration . tauto"eri8ation _____ 11. What is the incorrect na"e for the following co"pound ?) C&' C&C&- C&'A. 14!-di"ethyloxideB. !4'-epoxy butane C. 14!- i"ethylepoxide . all of these_____ 1!.Which reagent#s% would acco"plish the following reaction ?.)'&)&A. &!)4 &,B. -a)&/&'), C. ?iAl&0. C&';gBr/&!) _____ 1'. Which of the following reagent#s% used for al+ylationprocess of ben8ene?

A. C&'Cl/AlCl' B. C&';gBr/ether/&!) C. ;n)0(/&!)/heat . -B./CCl0_____10. Which of the following reagent#s% provides the following conversion. CHOC& - C&')&A.C&'C))&/&,B. ;n)0(/ &!)4 heat C.C&'C)Cl /AlCl' . none of these_____15. What is the product of the following reaction?'C))&C&))&@CC)B.C..A.PART II -Nomenclature( 20 points )a) Write the correct 2A@AC na"es. )& )&

)C&!-C&' )C&')C&' )& %#)%0) %C) %*)%E)#. 1111111111111111111111111111 0. 11111111111111111111111111111 C. 1111111111111111111111111111 *. 11111111111111111111111111111E.11111111111111111111111111111111b)Write the correct structures . tert-butylalcohol '-isopropyl-1-hexanol ethyl"ethyldisulfideBBBBBBBBBBBB

'40-di"ethyl-1-pentanol !-"ethyltetrahydrofuran0PARTT III- REACTIONS( 20 points)What "aCor product#s% would you expect fro" the following reactions?a% &-)'/&!.)0b%.)',&!.)0 c% AlCl'Cld% Cl-a -&! / -&' e% D;n)0/&!)/heatf%

.)Cl!/pyridine)&C&'g% -)!C)-C&'-aB&0/ether&'),

h%5 1% >C)'&/C&!Cl!&')!%1% C&'C&!;gBr/etheri%C&'-C&!- C&)!% &!)C% PART IVS!NT"ESIS (#$ points )a% What is the best procedure for preparing the following co"pound fro" ben8ene? # re*uires "ore than one step%)C&' b% 2dentify the structures for the co"pounds A4 C4 4 E and 1.Compound (A) + CH3Cl / AlCl3CH3KMnO4water / heat(C)CH3CH2OHacid(D)LiAlH4reduction()+( ! )c% 2llustrate the "echanis" for acid cataly8ed dehydration of 1-"ethylcyclohexanol. Be sure to use curved arrows#electron flow% for co"plete credit.6%onus &uestion (#0 points)@ropose a plausible structure and for a C1