UP Academic League of Chemical Engineering Students (UP ALCHEMES) Academics Afairs Afairs Committee Review and Tutorials Program, Program, AY 2012-2013 Chem 31 irst !"am #$A%P&! !'A%( SOURCES: Chem 31 Sample Exams (dated 15 January 2005, 29 July 200, 2 !ay 200", and 23 July 200"#
)* %+&T)P&! C)C!. /rite the letter o the est answer eside the numer o the item*
1* An acidic isomer o C *
A*
4*
C*
5*
or items 2-6, consider the structure o vitamin C. , , ,, C7 ,- C1 C2 C3 C C C6 , , , -, ,-
2* )denti8 the h8ridi9ation o C 6* A* s: 4* s:2 C* s:3 5* : 3* ow man8 C-C onds are there in the structure o vitamin C; A* 10 4* C* 7 5* < * /hat is the a::ro"imate ond angle o C 3-C-C6 onds; A* 120= 4* 10>*6= C* 1<0= 6* /hich is the most :olar ond; A* - 4* C- C* C-C C-C 5* C?C C?C
5* 260=
-,
A*
-, * /hich is the most acidic; 4* C3 C*
5* all o these
7* /hich o the ollowing statements regarding al@anes are TR+!; )* The8 react with o"8gen :roducing caron dio"ide and water* ))* The8 undergo ree radical halogenation in the asence o light* )))* The8 are insolule with water ut solule in non-:olar solvents such as toluene* )* The8 undergo nucleo:hilic sustitution in the :resence o + light* A* ) and )) 4* ) and ))) C* )) and and ) 5* ))) and ) <* C8clo:ro:ane is ver8 unstale :rimaril8 due to. A* steric strain strain 4* angle strain strain C* torsional torsional strain 5* none none o these >* The staggered conormation o al@anes is more stale than ecli:sed ecause o the asence o. A* angle strain strain 4* steric strain C* torsional torsional strain 5* none none o these
10* The meth8l grou:s o $%s-1,2-dimeth8lc8clohe"ane in the chair orm will have a conBguration o. A* euatorial, euatorial 4* a"ial, euatorial C* A D 4 5* none o these 11* /hat al@ene will 8ield C-C, C 2, and CC 2C3 u:on o9onol8sis ollowed 8 En, 2, F; A* C2?CC2C2C?C2 4* C 3C?CC?CC 3 C* C2?CC?CC 2C3 5* C2?CC?CC?C 2 12* /hat is the :roduct ormed when #C 3(2CC?C 2 undergoes acid-catal89ed h8dration; A* #C3(2CC2C2 4* C3C2CC3C3 C* #C3(2CCC 3 5* all o these 13* /hat is the :roduct ormed when C 3CGC undergoes catal8tic h8dration; A* C3CC3 4* C3CC 3 C* C3C2C? 5* C3C2C3 1* ow man8 mono-rominated :roducts will 2,-dimeth8l:entane give u:on reaction with 4r 2 under + light; A* 1 4* 2 C* 3 5* 16* The :i electrons o an al@ene act as the HHHHH in an electro:hilic addition reaction* A* electro:hile 4* ree radical C* nucleo:hile 5* none o these 1* /hich o the ollowing reactions o 2-utene will IT ollow %ar@ovni@ovJs rule; A* Reaction with 2, 2$ 4* Reaction with 4 3, then with -, 22, 2 C* Reaction with Cl 5* All will ollow %ar@ovni@ovJs rule 17* 2-ut8ne F HHHHHHH $%s-2-utene A* 2, &indlarJs catal8st 4* 2, Pt C* Ia in liuid I 3 5* none o these 1<* /hat is the :roduct o the reaction o 1-meth8lc8clohe"ene and 4r; A* 1-romo-2-meth8lc8clohe"ane 4* 3-romo-1-meth8lc8clohe"ene C* 1-romo-1-meth8lc8clohe"ane 5* -romo-1-meth8lc8clohe"ene 1>* /hich o the ollowing is a chain termination ste:; A* AK F 4K A4 4* AK F 4 A F 4K C* A 2 AK 5* none o these
20* /hich o the ollowing is the most stale al@ene; A*
4*
C*
21* The intermolecular orce involved in liuid utane is. A* Covalent onding 4* -onding C* an der /aals 5* 5i:ole-di:ole 22* The ecli:sed conormation o n-utane at C 2-C3 elow is unstale due to. H
CH3
H
A* Torsional and steric strain C* Angular and steric strain
4* $teric strain onl8 5* Torsional and angular strain
23* )n the more stale conormation o the c8cloal@ane elow, the numer o meth8l grou:s in the a"ial :osition is. ,3C C,3
C,3
A* 3
4* 2
C* 1
5* 0
CH CH3
2* /hich o the ollowing com:ounds would e the most stale ree radical; C
CH2
CH3
A*
CH3 H
H3C H
H
H
H
4*
H3C
CH3
C*
H
H
CH3
26* The order o decreasing stailit8 or the ollowing al@enes elow is.
A A* AL4LC
4 4* 4LALC
C* CL4LA
C 5* 4LCLA
))* 5raw at the ac@ o this :age what is descried 8 each item* 1* The C 612 isomer with the lowest oiling :oint* 2* The most stale C 12 al@ene* 3* The aworth :roMection o $%s-1,-dimeth8lc8clohe"ane* * The most stale conormation o $%s-1,-dimeth8lc8clohe"ane* 6* Possile termination ste: in the ree radical chlorination o C * )))* Provide the missing starting ma terial, reagents, intermediate, or :roduct in each o the ollowing reactions* 4 r2 h ν
1
2
#intermediate(
#%aMor :roduct(
6
2 2
2
7
4 2
F
3
2
#intermediate(
#%aMor :roduct(
)
I a , 2 1(
3
2 ( #C 3 ( 2 $
21 C
C
H
H
22
H
C H
CH
4 2
2
F
C
1<
1> F 20
#intermediate(
#:roducts(
2
16
2
1
I a , 2
CH
e " c es s 4 r
17
O
12
1(
O
F
3
2( E n
-
I
2
10
H
12
11
1(
3
2 ( 2
13