UNIVERSITI TEKNOLOGI MARA ARAU, PERLIS.
FACULTY OF APPLIED SCIENCE BACHELOR IN CHEMISTRY AS 202 CHM 624 (ADVANCED ORGANIC CHEMISTRY) EXPERIMENT 2 : PREPARATION OF 4-BROMOBENZOPHENONE BY THE FRIEDEL-CRAFTS REACTION
NAME: NIK ABDUL ABDUL AZIZ B. NIK ABD. RAHMAN MATRIX NUMBER: 2012457828 LAB PARTNER : OURSE : HM !2 !24 "A "ADVANED OR ORGANI H HEMISTR#$ GROUP: ASB5B% DATE O& EXPERIMENT 'AS DONE : 17 () MARH 2014 LETURER NAME : DR. PM. RAZALI
OBECTIVES
T* +-+- 4/B**-3*+)-*- ()- &-6-/(9 R-%(*.
T* -9- ()- +-%-(;- -6 * 4/B**-3*+)-*-.
INTRODUCTION
E-%(*+)% *(% 99(((* -%(*9 -(- --%(*+)- -+%; )6*;- (* *(% %*+*6 6 % * -< %*/%* *6 6*- <() --%(*+)% %* 9+-%-9. S%) -%(*9 <-- 69%*=--6 1877 )-9 &-6- 6 (9 6 - %*-%(=- >*< 9 &-6-/(9 -%(*9. T)- (*6%(* * % ;*+ (* *(% ; 9 %%*+9)-6 --%(*+)% 99(((* ()- % * "R?O@$ ;--(-6 ()- -%(* -(<-- % )6- 6 %)*6-. I **-3--, ()- -3-- 9 6-%(=(; 6 ortho, para/6-%(; 99((-(. H*<-=- ()9 -%(* ;=-9 ()- para/9*-, +-9 ortho/99(((* <)%) ;)( 9* - -+-%(-6 9 9(-% -99 =*-6. T)9 --%(*+)% *(% 99(((* *(% *<9 ()- 9()-99 * **%(-6 +*6%(9 * ()- -%(* -(<-- --9 6 % %)*6-9 * )66-9. T)- +*6%(9 - 6-%(=(-6 6 6* *( 6-;* 9-%*6 99(((*. B9%, 9(*%)*-(% *( * ()- L-<9 %6 %(9( 9 --6 -%9- *() ()99((- 6 ()- +*6%( * %*+--9. T)- &-6-/(9 >(* ;=- +*>(-6 +*6%(9. H*<-=-, ()- &-6-/(9 %(* 9 =- (-(=-.
E!UIPMENT AND INSTRUMENTS • • •
S(- () R*( -=+*(* I-6 S+-%(*9%*+ "IR S+-%(*9%*+$
MATERIALS • • • • • • • •
B**-3-- "&' 157.0$ B-3* %)*6- "&' 140.!$ A)6*9 %)*6-, "AC$ S*6 )6*6-, NOH "10$ D-() -()- L;)( +-(*- "!0/80F$ M;-9 9(-, M;SO4 +H 6%(* ++-
2.0 L, C.0 ; "1 *$ C.C L, 4.0 ; "C0 *$ 4.0 ; "C0 *$
PROCEDURES
P-+(* * 4/B**-3*+)-*
2 L * **-3-- <9 -6 <() C.C L * -3* %)*6- 50 L %*% 9>. T)-. 4.0 ; * AC <9 66-6 ()-- +*(*9. P* (* ()- 66(*, ()- %*%
9> <9 9)>-6 6 9(-6 (* (. T)- 9> <9 )-(-6 * 20 (-9 *; <(- (). A(- )-(; 6*-, ()- 6> -6 6 <9 %**-6 6 +*-6 *(* %- 6 ()- -; %*(-(9 <9 <9)-6 *( %- 66(* * 10 NOH (* ()- 9>. "(* 699*=-
-3*% %6 +-9-( 6 9* 9(9$ T)-, ()- 9*(* <9 -)-(-6 * -< (-9. H- 9*(* <9 -*=-6 6 ()- *< * +-%+((-6 <9 %*-%(-6. T)- *< 9*6 *(-6 <9 -( 699*=- <(- <() 66(* * NOH 6 -()-. T)- (- <9 -(%(-6 <() -()- * C (-9, ()- *;% -(%( <9 6-6 *=-
M;SO4 6 ()- -()- <9 -*=-6 * ()- *( -=+*(*. 4/B**-3*+)-*- --6 6 -%9(3-6 * ;)( +-(*- (* ;=- %**-99 9*6. T)- -6 6 -(; +*( * ()- +*6%( <-- -%*6-6. T)- +*6%( <9 3-6 <() IR 9+-%(*9%*+.
RESULT
M99 * <-;); ++-
0.1!C! ;
M99 * +*6%( @ <-;); ++-
0.!007 ;
M99 * +*6%(
0.!007 ; 0.1!C! ; 0"4#$% &
O'*+,./: S*6 * "%9($, *< %**
CALCULATIONS
Mol of bromobenzene =
¿
mass molar mass
3.0 g 157.0 g
/ mol
¿ 0.0191 mol ( limiting reactant ) Mol of benzoylchloride =
¿
mass molarmass
4.0 g 140.6 g / mol
¿ 0 . 0284 mol
P*/13 , M/535,* /*5, M/5,* , M5.& 7/. A3,5 8.51
4/B**-3*+)-*1CHBO 2!1.11 ;* 82F 0.4C71 ;
Theoretical yield =
261.11 g
mol
× 0.0191 mol
¿ 4 . 9872 g
Percentage yield =
¿
0.4371 g 4.9872 g
actual yield × 100 theoretical yield
× 100
¿ 8 . 76
DISCUSSIONS
I ()9 -+--(, 4/**-3*+)-*-, <9 9%%-99 *(-6 * ()- &-6-/ (9 %(* -%(* <)- **-3-- <9 -%(-6 <() -3* %)*6- <() +-9-%* 9(*; L-<9 %6 AC.
A%(* * B**-3--
T)- +-%-(;- -6 %%(-6 * ()- -%(* <9 8.7! <)%) 9 =- 9. T)9 <9 *<- 6- (* ()- %( ()( * ()- %9(9 9(%> ()- 9> 6 %*6 *( -*=- ( * <-;);. B-96-9 ()(, ()- *<- +-%-(;- -6 9 - 6- (* *99 6; -(%(* <() -()- * ()- -(%(* +*%-99 <9 *( %*+-(-. I 66(*, ()9 -+--( <9 9++*9-6 (* 9- *( -=+*(* (* -*=- ()- 9*=-( ( ()- , ()- *( -=+*(* <9 *( %(*; <- 6- (* -%)% +*-9. S*, <- 9-6 %*=-(* -()*6 (* -*=- ()9*=-( 9-(+ ()- <(- () 9; )*( +(- 6 -9-6 ()- (-+-(- (* ()- 9+-%% (-+-(- ()( <- --=- ()- 9*=-( < -9%+- *(. '- 99-, (- -%)-6 ()(-+-(-, ()- 9*=-( - -9%+-6 *( 6 * +*6%( -( ()- 9>. T)9 9 *( () +*+- < 6 -%-( -*=; * ()- 9*=-(. D- (* ()9 ((*, <- --=- ()9 9 ()- -9* * <) * -6 9 (** ((-. O()- () ()(, )-(; +*%-99 9( - -%*9-6 (* =*6
()- -=+*(*
* ()- +*6%( (9- -%9- ()- -(;
+*( * 4/
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
S*, <- 9- ()- * )-(; +*%-99 9; )*( +(- (* -*=- * -=+*(- ()- 6-() -()-. M- ()9 (-%)- 9 *( 9(- 6 -%9- * ()( <- 66 *( ;- (* %*+-(- -*=- ()- -()-. T)9 % - +*=-6 ()- IR 9+-%( <)%) 9)*< ()( ()-- 9 +-9-%- * -()- "%*)*$ ()- +*6%(. K-(*- 9++*9-6 (* )=- IR 9*+(* ( ;- * 1!80/1750 %/ 1
( ()- 9*+(* <9 *6 1!50/1700 %/1. S*, <- 99-6 ()- +*6%( *(-6 )9
%(* ;*+ * >-(*- 6 9 +-> ()- 9+-%( <9 99-6 (* -*; (* (. T)- +-> *(-6 9 =- 9 6- (* 9 +-%-(;- * +*6%( *(-6. P-9- 9-- ()- IR 9+-%( ((%)-6 (*;-()- <() ()9 -+*( * 6-(-6 (-+-((* * ()- 9+-%(.
C/35./:
&* ()- -+--(, ()- +*6%( *(-6 <9 4/**-3*+)-*-. T)- +-%-(;- -6 %%(-6 <9 8.7! 6 ()- -(; +*( *9-=-6 <9 *( 80F.
REFERENCES
P=, L+, K3, E;-, Introduction to Organic Laboratory Techniques A Smale Scale Approach, T)*9* B**>9*- P9)-9, C6 -6., 200.
)((+:<-**>.9(.;*=%;%**>.%;JID10754!M9>80IR/S+-%
E;- R. G., K3 G. S., L+ G. M., P= D. L., Introduction to Organic Techniques- A Small Scale Approach”, C6 E6., B**>9*- -%;- L-; , 6, 2011.
