MATERI MATERI PELENGKAP PELENGKA P RPP 3.9/4.9: 3.9/4 .9: SENYA S ENYAW WA KARBON BERGUGUS FUNGSI TABEL : GUGUS FUNGSIONAL SENYAWA KARBON CONTOH RUMUS NAMA
GOLONGAN
GUGUS FUNGSIONAL
RUMUS UMUM
Alkanl
! OH
C nH"n#" O
CH3CH"OH
E$anl
E$%&
!O!
CnH"n#" O
CH3!O!CH3
'()%$(l %$%&
CnH"nO
O // CH * C * H
E$anal
Alkanal
! CHO
Alkann
O // !C! O // ! C ! OH
A-a) Alkana$
O // ! C*O!
E-$%&
O // CH3 * C * CH 3
P&+ann ,a-%$n
CnH"nO"
O // CH3 ! C * OH
A-a) E$ana$ ,a-a) 0ka
CnH"nO"
O // CH3! C*O* CH3
M%$(l %$ana$
CnH"nO
5.1 ALKOHOL DAN ETER
Alk1l 2an %$%& )%)+0na( &0)0- 0)0) an -a)a a($0 C nH"n#" O. Alk1l Alk1l )%&0+akan -%na5a -%na5a an -%&(n k($a 60)+a( 2ala) k%1(20+an -%1a&(!1a&( 2an k($a 0nakan -%7aa( +%la&0$ 2an an$(-%+$(k. Alk1l an k($a k%nal 2an 2(+%&2aankan 2ala) kn-%n$&a-( 8 2an 9; )%)+0na( &0)0- CH 3CH"OH. S%2ankan %$%& an k($a 60)+a( 2ala) +%&2aanan $%&0$a)a 2(%$(l %$%& ,CH 3!CH"!O!CH"!CH3 2(0nakan -%7aa( 7a$ 7(07(02an +%la&0$. 5.1.1 Alkohol
Alk1l 2a+a$ 2(ana+ -%7aa( $0&0nan a(& 7(la -a$0 a$) 1(2&%n 2a&( )l%k0l a(& 2(an$( l%1 -0a$0 00- alk(l. Alk1l 60a 2a+a$ 2(ana+ 2a&( $0&0nan alkana 2()ana -a$0 a$) H 2a&( alkana 2(an$( 00- OH. Ol%1 ka&%na ($0 -(
Alk1 Alk1ll +&()% +&()%&& Alk Alk1 1ll -%k% -%k%n2 n2%& %& Alk1l $%&-(%&
: G00G00- *OH $%&(ka $%&(ka$$ +a2a +a2a a$) a$) C +&()%& +&()%& : G00 G00-- *OH *OH $%&( $%&(ka ka$$ +a2a +a2a a$) a$) C -%k0 -%k0n2 n2%& %& : G00- *OH $%&(ka$ +a2a a$) C $%&-(%&
B%&2a-a&kan $%&(ka$na 00- *OH +a2a 6%n(- a$) C= alk1l 2(7%2akan )%n6a2( :
-
Alk Alk1 1ll )n )n> >al al%n %n Alk1l 2(>al%n Alk1l $&(>al%n Alk Alk1 1ll +l +l(> (>al al%n %n
: : : :
)%n )%n(k (ka$ a$ -a$0 -a$0 00 00-- OH= OH= CH 3CH"OH ,%$anl )%n(ka$ 20a 00- OH= CH "OH!CH"OH ,%$ana2(l )%n(ka$ $(a 00- OH= CH "OH!CHOH!CH"OH ,l(-%&l )%n )%n(k (ka$ a$ 00 00-- OH l%7( l%7(1 1 2a&( 2a&( 3= CH "OH * ,CHOH n * CH"OH
1. TATANAM TATANAMA A SENYA SEN YAW WA ALKOHOL ALKO HOL
Ka&%na alk1l 2a+a$ 2(ka$akan -%7aa( $0&0nan alkana= )aka a&a )%)7%&( na)a -%na5a (n( -%-0a( 2%nan +%)7%&(an na)a -%na5a alkana 2%nan )%nan$( ak1(&an *a 2%nan *l. Lanka1!lanka1 +%)7%&(an +%)7%&(an na)a -%na5a alk1l a2ala1 -%7aa( 7%&(k0$. ?. P(l(1la1 P(l(1la1 &an$a( &an$a( $%&+an6an $%&+an6an 2a&( &0)0&0)0- -$&0k$0& -$&0k$0& -%na5a -%na5a $%&-%70$ $%&-%70$ an )%n(ka$ )%n(ka$ 00- <0n-( <0n-( OH. ". P%)7%&(an P%)7%&(an n)& n)& 0&0$ a$) C +a2a +a2a &an$a( ka&7n ka&7n== -%2%)(k(an -%2%)(k(an &0+a &0+a -%1(na -%1(na a$) C an an )%n(ka$ )%n(ka$ 0000<0n-( )%n2a+a$ n)& 0&0$ $%&k%(l. ?@Pa%
Cn$1: CH3OH M%$anl
CH3CH"OH %$anl
CH3!CHOH!CH3 "!+&+anl
CH3!CH"!CH"OH ?!+&+anl
Kegiatan 1 :
?. '%nan '%nan )%n )%n0na 0nakan kan )l )l)2 )2 70a$la 70a$la1 1 )2%l )2%l )l%k0l )l%k0l C 4H?O an )%nan20n 00- OH ,lnan alkanl R0-)0 -)0- -$&0k$0& : a. . . ...... ....... ....... ....... .... Na)a
:
.
R0-)0 -)0- -$&0k$0&
: 7. .
Na)a
:
................. 2
.
... ....... ....... ....... ....... .... ...................... ...
". T0l(-k T0l(-kan an &0)0&0)0- -$&0k$0& -$&0k$0& -%na5a -%na5a alk1l alk1l an an na)ana na)ana $%&an$0) $%&an$0) 2(7a5a1 2(7a5a1 (n(: a.
"!)%$(l!?! !?!70$anl
: . ..
7. 3!)%$(l!"!+%n$anl 3!)%$(l!"!+%n$anl
: ..
.
: ..
"!%$(l!?!70$anl
2. "!%$(l!"!) "!%$(l!"!)%$(l!? %$(l!?!+%n$ !+%n$anl: anl: %.
3=4!2( 3=4!2()% )%$(l $(l!?! !?!+%n +%n$an $anl l : . ... ..
3. 'a&( -%na5a -%na5a!-%n !-%na5a a5a an an2a an2a +%&l%1 +%&l%1 +a2a -al n)& n)& ? 2an " k%l)+kk k%l)+kkan an +a2a 6%n(6%n(- alk1l alk1l +&()%&= +&()%&= -%k%n2%& 2an $%&-(%&. Alk Alk1 1ll +&() +&()%& %& : ... ..... ..... ... Alk1 Alk1ll -%k0n2 -%k0n2%& %&
: .... ........ ....
Alk Alk1 1ll $%&$%&-(% (%&&
: ... ..... ..... ...
2. Sifat!ifat Alkohol a.
S(
Na)a T&(>(al T&(>(al M%$(l alk1l E$(l alk1l n!+&+(l alk1l I-+&+(l alk1l n!70$(l alk1l S%k. B0$(l alk1l I-70$(l alk1l T%&-(%& 70 70$(l al alk1l
R0)0CH 3OH CH 3CH"OH CH 3CH"CH"OH CH 3CHOHCH3 CH 3,CH""CH"OH CH 3CHOHCH"CH3 CH 3CH,CH3CH"OH ,CH 3"COHCH3
T($(k 2(2(1 2(2(1 , C 4=; 8=3 98=" "=3 ??8=8 99=; ?8=9 "=
". Sifat fat Ki Ki#ia
?. Alk1l Alk1l 7%&%ak7%&%ak-(( 2%nan 2%nan la) na$&(0) na$&(0) )%n1a-( )%n1a-(lkan lkan aa- 1(2&%n 1(2&%n "@Pa%
"ROH # " Na
"RONa
#
"CH3CH"OH # "Na
H" "CH3CH"ONa # H"
". B%&%ak-( 2%nan PD3 2an PD; 3 ROH # PD3
3 RD
#
3 CH3CH"OH # PCl3
H3PO3 3 CH3CH"Cl # H3PO3
3. Alk1l 2a+a$ 2(2%1(2&a$a-( l%1 H "SO4 +%ka$ a. +a2a -010 ? C )%)7%n$0k alk%na 7. +a2a -010 ?4C )%)7%n$0k %$%& 1$% &
CH
o
n
"n
ROH # H "SO4 +%ka$ 1'%o& ROR 1$%o&
CH" CH" # H"O
CH3CH"OH # H"SO4 +%ka$ o
1'% & &H(&H2O&H2&H(
) H"O
4. 'a+a$ 2(k-(2a-( ,alk1l +&()%& +al(n )02a1 $%&k-(2a-( )%)7%n$0k alkanal= alk1l -%k%n2%& )%)7%n$0k k%$n 2an alk1l $%&-(%& +al(n -0ka& 2(k-(2a-(. Ok-(2a-( alk1l $%&-(%& 2%nan k-(2a$& k0a$ akan )%n%7a7kan +0$0-na &an$a( ka&7n a. k-(2a-( alk1l +&()%& )%)7%n$0k al2%1(2= 2an &%ak-( k-(2a-( akan 7%&lan60$ -a)+a( $%&7%n$0k a-a) ka&7k-(la$. ROH # k-(2a$&
R!CHO
CH3CH"CH"OH # k-(2a$&
R!COOH CH 3CH"CHO
CH3CH"COOH
7. Ok-(2a-( alk1l -%k0n2%& akan )%n1a-(lkan k%$n an -0ka& 2(k-(2a-( l%7(1 lan60$. O // ROH # k-(2a$& R!C!R OH
O // CH 3 * C ! CH3
CH3! CH * CH3 # k-(2a$& .
Alk1l $%&-(%& -0ka& 2(k-(2a-( OH
R * C * R # k-(2a$&
$(2ak 7%&%ak-(
R ,CH3" * COH * CH 3 # k-(2a$&
$(2ak 7%&%ak-(
;. Alk1l 7%&%ak-( 2%nan a-a) ka&7k-(la$ )%)7%n$0k %-$%& ROH # RCOOH
RCOOR
#
CH3CH"OH # CH3COOH
H" O CH3COOCH"CH3 # H"O
. B%&%ak-( 2%nan a-a) 1al(2a ,HD )%)7%n$0k RD ROH # HCl
R!Cl
#
H"O
CH3CH"OH # HCl
CH3CH"Cl # H"O
8. B%&%ak-( 2%nan H"SO4 +%ka$ 7%&a-a+ a$a0 HNO 3 )%)7%n$0k %-$%& an&an(k ROH # HOSO3
CH3CH"OH # HOSO 3H
ROSO3H
#
H"O
CH3CH"OSO3H # H"O 3@Pa%
ROH # HONO"
RONO"
CH3CH"OH # HONO "
#
H"O
CH3CH"ONO"
# H"O
(. *e#"+atan alkohol E$anl -%a&a ala)( 7anak $%&2a+a$ +a2a 70a1!70a1an an $%la1 )a-ak= ak(7a$ <%&)%n$a-( ka&71(2&a$. Ol%1 ka&%na ($0 alk1l 2a+a$ $%&7%n$0k 2a&( +&-%- +%&a(an 2ala) +%)700a$an $a+% C?"H""O??
CH?"O
+%&a(an
" C"H;OH # CO"
P%&a(an akan 7%&1%n$( 6(ka ka2a& alk1l $%la1 )%na+a( ka2a& ?4 1(na ?. (ka 2((n(nkan ka2a& an l%7(1 $(n(= a)+0&an ($0 1a&0- 2(-0l(n. Ha-(l +%n0l(nan )%&0+akan a%$&+ 9; alk1l 2an ; a(&. Un$0k )%n1a-(lkan alk1l +%ka$ ,9 a$a0 alk1l a7-l0$ ,? k% 2ala) a%$&+ 2($a)7a1kan CaO 0n$0k )%na&(k a(&. '. Keg+naan alkohol
E$anl 2ala) k%1(20+an -%1a&(!1a&( 2(0nakan -%7aa( +%la&0$= 7a$!7a$an 2an 7a1an 7aka&. Alk1l 8 7(a-a 2(0nakan 0n$0k 2(-(n<%k$an= la&0$an (2(0) 2ala) alk1l ,(2(0) $(n$0&% 2(0nakan -%7aa( 7a$ l0ka. Alk1l $%1n(- an $%la1 2(&a0n( )%$anl 2an k($a k%nal -%7aa( -+(&($0- 2(0nakan -%7aa( +%la&0$ a$ ,+l($0& 2an -%7aa( 7a1an 7aka&. M%$anl 7anak 2(0nakan -%7aa( +%la&0$ 2ala) +%)70a$an +%&n(- 2an lak -%&$a -%7aa( +%)7%&-(1 ka&a$ +a2a la)!la). T($(k 7%k0 an &%n2a1 )%n%7a7kan )%$anl 2(0nakan 0n$0k a)+0&an an$( 7%k0 +a2a )7(l 2( 2a%&a1 2(n(n. Alk1l ka2a& &%n2a1 , -a)+a( 2%nan ?; 7anak $%&2a+a$ 2ala) )(n0)an &(nan -a)+a( )(n0)an k%&a- G&%%n San2 )%nan20n ? alk1l 2an 7(& )%nan20n ?; alk1l. Alk1l an 2(kn-0)-( )an0-(a akan 2(%&na 2an 2(k-(2a-( $%&0$a)a 2(2ala) 1a$( ,l%>%& 2%nan +%&$lnan %n()% an 2(-%70$ alk1l!2%1(2&%na-%. P&20k 2%1(2&%na-% (n( a2ala1 a-%$al2%1(2= CH 3CHO 2an k-(2a-( 7(l(- )%$anl )%n1a-(lkan <&)al2%1(2 an 7%&-(
;.?." ETER 1. R,M,S ,M,M
E$%& 2($0n60kkan l%1 00- C * O * C= -%na5a!-%na5a (n( 7(a-ana 2(7%&( na)a 2%nan +%&$a)a!$a)a )%n%70$kan k%20a 00- alk(l a$a0 a&(l an $%&(ka$ +a2a a$) k-(%n 2an k%)02(an 2($a)7a1 ka$a %$%&. B(la k%20a 00- alk(l a$a0 a&(l -a)a )aka a5alan 2( -%&(nkal( $(2ak 2(0nakan CH3 * O * CH 3 CH3 * CH" * O * CH" ! CH3 CH3 * CH *O ! CH3 '()%$(l %$%& 2(%$(l %$%& )%$(l (-+&+(l %$%& ,)%$(l %$%& ,%$(l %$%& CH 3 Ka&%na %$%& )%&0+akan $0&0nan alkana= )aka $a$a na)a %$%& 60a 2a+a$ 2($0&0nkan 2a&( na)a alkana -%2ankan 00- alkk-( ,! O * R 2a+a$ 2(ana+ -%7aa( a7an ,R 2%nan &an$a( C l%7(1 +an6an 2(ana+ -%7aa( &an$a( 0$a)a alkana. R O R Alkana alk(l
CH3 O CH 3 M%$k-( )%$ana
R J R alkk-( alkana
CH3 O CH " CH3 )%$k-( %$ana
CH3 CH" O CH" CH3 %$k-( %$ana
Un$0k l%7(1 )%n%nal a&a )%)7%&( na)a -%na5a %$%& $0l(-kan na)a -%na5a!-%na5a %$%& 2( 7a5a1 (n(: CH3 * O * CH" * CH" * CH3
CH3 * O * CH * CH 3
CH3 CH3
CH3 * O * CH * CH3
4@Pa%
CH3 2. -e"ea/a !ifat 0an keg+naan ete
S(
'. !o#e /a0a alkohol 0an ete. '(k%nal 7%7%&a+a 6%n(- (-)%&= an$a&a la(n (-)%& -$&0k$0& ,+-(-(= &an$a( 2an 00- <0n-( 2an (-)%& +$(k. Pa2a (-)%& 00- <0n-( $%&2a+a$ +%&7%2aan 00- <0n-( a$= )(-alna an$a&a alk1l ,!OH 2%nan %$%& ,!O!= S%2ankan +a2a (-)%& &an$a( $%&2a+a$ +%&7%2aan &an$a( 0$a)a 2an +a2a (-)%& +-(-( 2($0n60kkan l%1 l%$ak a7an a$a0 l%$ak 00- <0n-( 2ala) &an$a( 0$a)a. T%la1 2(k%$a10( 7a15a a$) ka&7n )%)+0na( %)+a$ %l%k$&n >al%n-( an $%&a&a1 k% -020$!-020$ -0a$0 $%$&a1%2&n. (ka k%%)+a$ >al%n-( ($0 )%n(ka$ %)+a$ a$) a$a0 k0)+0lan a$) an 7%&la(nan= )(-alna "!70$anl 2($%)0kan 20a -0-0nan )l%k0l -%7aa( 7%&(k0$:
K%20a -0-0nan )l%k0l ($0 7%&7%2a ka&%na -0-0nan an -a$0 )%&0+akan 7aanan %&)(n 2a&( -0-0nan k%20a an $(2ak 2a+a$ -al(n 7%&()+($. P%&7%2aan an$a&a k%20a -0-0nan )l%k0l (n( akan 6%la$%&l(1a$ 7(la 2(0nakan )2%l )l%k0l ,)l)2. Ka&%na k%20a -0-0nan )l%k0l 7%&la(nan = 7%&a&$( k%20a )l%k0l $%&-%70$ 7%&la(nan. '%)(k(an +0la k%20a -%na5a )%n0n60kkan -(. S0a$0 -%na5a 2a+a$ 2(ka$akan 7%&(-)%& +$(k 6(ka -%na5a $%&-%70$ )%)+0na( atom C asimetris (atom C khiral) yaitu atom C yang mengikat 4 gugus berlainan . Banak -%na5a an 2($%)0kan 2( ala) 7%&-(
%.
na)a : 7.
na)a : ... <.
na)a : .
...
... na)a : ...
.
... ;@Pa%
na)a :
na)a : ...
2. na)a : . 'a&( &0)0-!&0)0- 2(a$a- -%na5a!-%na5a )ana an )%n0n60kkan a2ana (-)%&: a.
00- <0n-(
.
7. P-(-(
.
.
Ran$a(
.
2. +$(k ak$(<
.
Un$0k )%)02a1kan 2an )%n1(n2a&( k%-ala1an 2ala) )%na&( (-)%&= an2a 1a&0- )%)a1a)( 60)la1 &an$a( -$&0k$0& an )0nk(n 2a&( alk(l: K%)0nk(nan &0)0- -$&0k$0& 2a&( alk(l n ? -.2 n ; 0)la1 a$) C
R0)0- alk(l
R0)0- S$&0$0&
0)la1 k%)0nk(nan
?
CH3 !
CH3 !
?
"
C"H; !
CH3 * CH" !
?
3
C3H8 !
CH3 * CH" * CH"!
"
CH3 * CH *
4
C4H9 !
CH3 CH3 * CH" * CH" * CH"!
4
CH3 * CH * CH" *
CH3 CH3 * CH" * CH *
CH3
CH3
CH3 * C *
;
C;H?? !
CH3 CH3 * CH" * CH" * CH" * CH"!
CH3 * CH" * CH" * CH * CH 3
CH3 * CH" * CH * CH" * CH3
CH3 * CH" * CH * CH" *
CH3 CH3 * CH * CH" * CH" *
CH3 CH3
CH3 * C * CH *
CH3 CH3
@Pa%
CH3 * CH" * C *
CH3 CH3
CH3 * C * CH" *
CH3 '%nan )%)+%&1a$(kan $a7%l $%&-%70$ 2a+a$ 2(k%$a10( (-)%& 2a&(: a. Alk1l R!OH= ka&%na R 2%nan n ; k%)0nk(nanna a2a )aka 60)la1 alk1l an )0nk(n a2a &0)0- -$&0k$0& alk1l. -%+%&$( +a2a $a7%l 2(a$a- ,n; +a2a $anan an k-n l%$akkan OH 7. E$%& R * O * R = 60)la1 n 2ala) R 2an R ; 2%nan k)+-(-(: n ? 2an n 4 60)la1 (-)%& an )0nk(n ? 4 n " 2an n 3 60)la1 (-)%& an )0nk(n ? " a2( 60)la1 (-)%& %$%&na . Cn$1: R ,n ? CH3 * O
R , n 4 * CH" * CH" * CH" * CH3 * CH" * CH * CH 3
CH3 * CH * CH" * CH3
CH3
CH3
* C * CH3
CH3 'a&( &0)0-!&0)0- 2(a$a- -%na5a!-%na5a )ana an )%n0n60kkan a2ana (-)%&: a.
00- <0n-(
.
7. P-(-(
.
.
Ran$a(
.
2. +$(k ak$(<
.
An$a&a alk1l 2an %$%& 2a+a$ 2(7%2akan 2a&( -(
R+#+! St+kt+
Titik 0i0ih
?! 70$anl
CH 3 * CH" * CH" * CH"OH
??8=8C
"! 70$anl
CH 3 * CH,OH * CH" * CH3
99=;C
"!)%$(l!"!+&+anl
CH 3 * C ,OH * CH 3
"=C
CH3 "!)%$(l!?!+&+anl
CH 3 * CH,CH3 * CH"OH
?8=9C
?!)%$k-( +&+ana
CH 3 * O * CH " * CH" * CH3
3=9C
"!)%$k-( +&+ana
CH 3 * O * CH * CH 3
3"=;C
CH3 E$k-( %$ana
CH 3 * CH" * O * CH" * CH3
34=;C 8@Pa%
P%&$anaan : a.
Baa()ana $($(k 2(2(1 alkanl 2(7an2(n 2%nan $($(k 2(2(1 %$%& 2%nan 60)la1 a$) C an -a)a ............................. .............................
7. Baa()ana 1070nan an$a&a $($(k 2(2(1 alkanl 2%nan: 7.?. %n(- alkanl ,+&()%&= -%k0n2%&= $%&-(%& .................... .................... 7."
Pan6an &an$a( 0$a)ana ....................
. S%na5a 2%nan &0)0- )l%k0l C 3HO 2a+a$ 7%&0+a alkanl 2an %$%&. (ka -%na5a 2()ak-02 a2ala1 -%na5a A = B= C 2%nan $($(k 2(2(1 7%&$0&0$!$0&0$ 98=" C= ?C 2an "=3 C. T%n$0kan -%na5a A= B 2an C an 2()ak-02. ............................. ............................. ". R%ak-( alk1l 2%nan 7%7%&a+a +%&%ak-( Alk1l 2an %$%& )%&0+akan (-)%& 00- <0n-(. S%la(n 2a+a$ 2(7%2akan )%lal0( -(
E$%& '%nan la) Na $(2ak 7%&%ak-(
a.
R * O * R # Na $(2ak 7%&%ak-( 7. '%nan PD3 $(2ak 7%&%ak-(
'%nan la) Na 7%&%ak-( )%n1a-(lkan a- 1(2&%n ROH # Na → RONa # H"
7.
'%nan +%&%ak-( PD 3 )%)7%n$0k RD 2an P,OH 3 ROH # PD3 → RD # P,OH3
a.
CH3!CH"OH#PCl 3→ CH3!CH"Cl #P,OH 3
. $(2ak 2a+a$ 2(k-(2a-(
.
'a+a$ 2(k-(2a-( Alk1l +&()%& 2(k-(2a-( )%n6a2( al2%1(2 Alk1l -%k0n2%& 2(k-(2a-( )%n6a2( k%$n Alk1l $%&-(%& -0ka& -%kal( 2(k-(2a-(= 2an 7(la 2(k-(2a-( 2%nan k-(2a$& k0a$ akan +%a1 )%n6a2( alkanal 2an alkann 2%nan &an$a( C l%7(1 +%n2%k
Soal Latihan ?. B%&(la1 na)a -%na5a!-%na5a an )%)+0na( &0)0- -$&0k$0& 7%&(k0$: a.
CH3!CH,CH3!CH"OH
2.
CH3 * CH" * O * CH,CH 3"
7. CH3 * CH" ! CH,OH * CH,CH 3"
%.
CH3 * O ! CH,CH3 *CH,CH3 * CH3
.
<.
CH3 * CH" * O * CH" *CH,CH3"
CH3 * CH" *CH" * CH,CH3!CH"OH
". T0l(-kan &0)0- -$&0k$0& -%na5a!-%na5a 2( 7a5a1 (n( a.
" )%$(l!?!70$anl
2.
)%$(l!(-+&+(l %$%&
7. 3 )%$(l!?!70$anl
%.
"!%$k-( +&+ana
.
<.
"!)%$k-(= "!)%$(l 70$ana
"=3 2()%$(l!"!70$anl
3. S0a$0 -%na5a )%)+0na( &0)0- )l%k0l C 3HO. S%na5a $%&-%70$ 7%&%ak-( 2%nan la) Na )%n1a-(lkan a- H ". (ka 2(k-(2a-( )%n1a-(lkan -%na5a C 3HO an $(2ak )%&%20k-( <%1l(n. T%n$0kan na)a -%na5a C3HO an 2()ak-02. ;.3
ALDEHD DAN KETON 'ala) +%)70a$an a5%$an 2( la7&a$&(0) 7(l( 2an 20n(a k%2k$%&an= -%&(n 2(0nakan <&)al(n. F&)al(n )%&0+akan la&0$an <&)al2%1(2 4 . F&)al2%2(2a $%&ln -%na5a alkanal ,al2%1(2 an )%)+0na( &0)0- HCHO. B(la a(& $a+% 2(k-(2a-( 2%nan 1a$(!1a$(= akan $%&7%n$0k al2%1(2 an @Pa%
)%)+0na( &0)0- CH3CHO. S%2ankan 0n$0k )%n1(lankan a$ k0k0 ,k0$%k= 0)0)na 2(0nakan a-%$n ,CH3COCH3. F&)al2%1(2 2an a-%$al2%1(2 )%&0+akan -%na5a al2%1(2= -%2ankan a-%$n a2ala1 n$1 2a&( -%na5a k%$n. ;.3.?
R0)0- U)0) P%&1a$(kanla1 &0)0- -$&0k$0& 2a&( k%$(a -%na5a al2%1(2 2an k%$n an -%&(n an2a 60)+a( -%1a&(!1a&( 2( 7a5a1 (n(. O O O @@ @@ @@ H!C!H CH3 ! C ! H CH3 * C * CH3 M%$anal %$anal a-%$n B(la an2a +%&1a$(kan k% $(a n$1 &0)0- )l%k0l 2( a$a-= 2a+a$ 2(ka$akan 7a15a al2%1(2 2an k%$n )%)+0na( 00- <0n-( ka&7n(l ,JC O. Pa2a al2%1(2 a$) C 2a&( 00- ka&7n(l $%&(ka$ +a2a -a$0 a$) 1(2&%n 2an -a$0 a$) C la(n. Pa2a k%$n a$) C 2a&( 00- ka&7n(l $%&(ka$ +a2a 20a a$) C la(n.
O // !C*C H
O
!C*C*C!
K%$n
al2%1(2
-%1(na &0)0- 0)0) al2%1(2 2an k%$n 2a+a$ 2($0l(- -%7aa(
O // R*C*H
O // R*C*R
Al2%1(2 ,alkanal
;.3."
K%$n ,alkann
Ta$ana)a Al2%1(2 2an K%$n
M%n0&0$ IUPAC= na)a -(-$%)a$(k -%na5a alkanal 2($0&0nkan 2a&( na)a 1(2&ka&7n -%7an2(n 2%nan )%nan$( ak1(&an *a 2%nan ak1(&an *al. S%+%&$( 7(a-a a$)!a$) ka&7n 2(7%&( n)& 7%&0&0$an 2()0la( 2a&( a$) ka&7n(l. Akan $%$a+( n)& -a$0 $(2ak +%&l0 2($0n60kkan= ka&%na 2ala) -%na5a! -%na5a al2%1(2 al((al. Na)a $&(>(al al2%1(2 2a+a$ 2($0&0nkan 2a&( na)a a-a) ka&7k-(la$ 2%nan )%nan$( ak1(&an a$ 2%nan ka$a al2%1(2. M(-alna= a-%$al2%1(2 ,2a&( a-a) a-%$a$. S%2ankan na)a $&(>(al -%na5a k%$n= 2%nan 6alan )%n%70$kan $%&l%7(1 2a10l0 00- alk(l an $%&(ka$ +a2a a$) C= 00- ka&7n(l= k%)02(an 2((k0$( 2%nan ka$a k%$n. Cn$1 7%7%&a+a -%na5a al2%1(2 2an k%$n:
O // H*C*H )%$anal <&)al2%1(2 O // CH3 * CH" * C * H +&+anal ,+&+(nal2%1(2 O // CH3 * CH * CH " * C * H
CH3 3!)%$(l= 70$anal
O // CH3 * C * H E$anal ,a-%$al2%1(2
O // CH3 * CH" * C * H +&+anal ,+&+(nal2%1(2
O // CH3 * C * CH3 P&+ann a-%$n
O // CH3 * C * CH" * CH3 B0$ann E$(l= )%$(l k%$n O // CH3 * C * CH * CH 3
CH3 "!)%$(l= "!+&+ann , )%$(l= (-+&+(l k%$n
9@Pa%
Un$0k l%7(1 )%)a1a)( a&a )%)7%&( na)a al2%1(2 2an k%$n= 2(-k0-(kan k%(a$an 2( 7a5a1 (n( ?. '%nan )%n0nakan )l)2 70a$la1 )2%l )l%k0l 2%nan &0)0- C 4HO. K%)02(an &0)0- -$&0k$0& an an2a +%&l%1 2an 7%&(la1 na)a -%na5a!-%na5a $%&-%70$. a.
.
na)a : ...
... na)a : ...
7. na)a : 'a&( &0)0-!&0)0- 2(a$a- -%na5a!-%na5a )ana an )%n0n60kkan a2ana (-)%&: a.
00- <0n-(
.
7. P-(-(
.
.
Ran$a(
.
2. +$(k ak$(<
.
5.(.(
*e#"+atan Al0ehi0 0an Keton
Al2%1(2 2a+a$ 2(70a$ 2%nan k-(2a-( alk1l +&()%&= -%2an k%$n 2a+a$ 2(+%&l%1 2a&( ak-(2a-( alk1l -%k0n2%&. O "! # C& "O8 # H // R * CH"OH R*C*H
"!
C& "O8 # H CH3 * CH" * CH"OH
#
O // CH3 * CH" * C * H O
"!
#
C& "O8 # H
// R * C * R
R * CH,OH * R
O "!
#
C& "O8 # H CH3 * CH,OH * CH 3
5.(.'
// CH3 * C * CH3
-e"ea/a Reak!i Al0ehi0 0an Keton
?. R%ak-( Ok-(2a-( Al2%1(2 )%&0+akan -%na5a an )02a1 )%nala)( k-(2a-( 2an )%)7%n$0k a-a) ka&7k-(la$. A2ana -%na5a al2%1(2 2a+a$ 2(06( 2%nan +%&%ak-( an 7%&-(
K%(a$an ?. S%2(akan " 70a1 $a70n &%ak-(. I-(la1 $a70n ? 2%nan ? )l la&0$an <&)al(n an )%nan20n ? <&)al2%1(2. ". I-(la1 $a70n " 2%nan " )l la&0$an a-%$n an $%la1 2(%n%&kan 2%nan +%&7an2(nan ?:?. 3. 'ala) k%20a $a70n 2($a)7a1kan " )l la&0$an F%1l(n ,la&0$an F%1l(n A 2an F%1l(n B 2a+a$ 2(a)+0& +a2a -aa$ 2(0nakan. 4. Pana-kan k%20a $a70n2ala) +%)ana- a(&. Mak-02na %l0+kan k%20a $a70n ($0 k% 2ala) 5a2a1 an 7%&(-( a(& +ana- 2( a$a- a+(. ;. Ulan( lanka1 ? -/2 4= $%$a+( )%n0nakan +%&%ak-( Tl%n- ,la&0$an +%&ak n($&a$ =? M an 2($a)7a1 la&0$an NH 3 +%ka$ -a)+a( 7%&l%7(1.
? @ P a %
". R%ak-( A2(-( a. A2(-( 00- ka&7n(l 2%nan a- H(2&%n ,&%20k-( 1a-(l a2(-( alkanal 2%nan 1(2&%n )%n1a-(lkan alk1l +&()%&= 2an a2(-( alkann )%n1a-(lkan alk1l -%k0n2%& O // R*C*H
# H"
O // CH3 * CH" * C * H P&+anal O // R * C * R
→ R * CH"OH alk1l +&()%&
# H"
→ CH3 * CH" * CH"OH alk1l +&()%& ?! +&+anl OH
# H"
→ R * CH * R alk1l -%k0n2%&
O // CH3 * CH" * C * CH" ! CH3 3!+%n$ann
OH
# H"
→ CH3 * CH" * CH! CH" * CH3 3!+%n$anl alk1l -%k0n2%&
R%ak-( (n( $%&ln &%20k-( ka&%na 2%nan +%na)7a1an )l%k0l 1(2&%n= 00- ka&7n(l 2a&( al2%1(2 )%nala)( &%20k-( )%n6a2( alk1l.
.
A2(-( alkanal a$a0 alkann 2%nan +%&%ak-( &(na&2 ,R!M!D. Alkanal 2($a)7a1 R! M! D k%)02(an 2(&%ak-(kan 2%nan a(&= )%)7%n$0k alk1l -%k0n2%&. S%2ankan a2(-( alkann 2%nan R * M * D 2(1a-(lkan alk1l $%&-(%& O O * MD // R * C * H # R * M * D → R * C * R
H O // CH3 * C * H # Cl * M * CH"!CH"!CH3
O * MCl
→ CH3 * C * CH " * CH" * CH3 H
O * M Cl
OH
CH3 * C * CH"!CH"!CH3 # H"O → CH3 * C * CH" * CH" * CH3 # M,OHCl
H
H
2. S%na5a alkanal 2an alkann 2a+a$ 2(a2(-( 2%nan a$ la(n -%+%&$( HD= HCN 2an H "O.
5.
ASAM KAR-OKSLAT
T%n$0 an2a -02a1 $(2ak a-(n la( $%&1a2a+ a-a) 0ka an )%)+0na( &0)0- )l%k0l CH 3COOH. A-a) 0ka )%&0+akan -%na5a a-a) ka&7k-(la$. A-a) ka&7k-(la$ an la(n a($0 -%na5a an $%&2a+a$ 2ala) $0701 -%)0$ -%1(na 2(k%nal -%7aa( a-a) -%)0$ a$a0 a-a) <&)(a$. A-a) -%)0$ )%)+0na( &0)0HCOOH. B(la an2a +%&1a$(kan &0)0- )l%k0l k%20a -%na5a a-a) $%&-%70$ 2a+a$ 2(ka$akan 7a15a a-a) ka&7k-(la$ )%nan20n 00- <0n-(nal ka&7n(l an )%n(ka$ 1(2&k-(l ,00- ka&7k-(l: !CO OH G00- ka&7k-(l $%&(ka$ +a2a 060n &an$a( C = -%1(na a-a) ka&7k-(la$ 2a+a$ 2(na$akan 2%nan &0)0- 0)0): R!CO ?? @ P a %
OH A-a) ka&7k-(la$ 2a+a$ 2(k%l)+kkan )%n6a2( 7%7%&a+a 6%n(- a($0 a-a) ka&7k-(la$ 6%n01= a-a) ka&7k-(la$ $(2ak 6%n01= a-a) 2(ka&7k-(la$= a-a) 1(2&k-(l ka&7k-(la$ 2an a-a) a)(n ka&7k-(la$ ,a-a) a)(n= +%n0-0n 0$a)a +&$%(n. A-a) ka&7k-(la$ 2%nan &an$a( l0&0- $%la1 la)a 2($%)0kan= $%&0$a)a 2a&( 1(2&l(-(- l%)ak an 7%&a-al 2a&( $0)701!$0)701an a$a0 1%5an. Ka&%na ($0 a-a) ka&7k-(la$ -%&(nkal( 2(-%70$ a-a) l%)ak. Na)a $&(>(al 2a&( a-a) ka&7k-(la$ 7(a-a 2($0&0nkan 2a&( -0)7%&na a$a0 )%n0nakan na)a a-a) alkana ka&7k-(la$. S%2ankan 7%&2a-a&kan a$0&an $a$ana)a IUPAC= na)a -%na5a a-a) ka&7k-(la$ 2a+a$ 2($0&0nkan 2a&( na)a alkana an -%-0a( 2(a5al( 2%nan ka$a a-a) 2an ak1(&an !a 2(an$( !a$. Un$0k l%7(1 )%)a1a)( $a$ana)a a-a) ka&7k-(la$ l%nka+( Ta7%l 2(7a5a1 (n( N
R0)0- S$&0k$0&
?.
O // H * C * OH
Na)a S(-$%)a$(k ,IUPAC
Na)a T&(>(al
A-a) )%$ana$
A-a) F&)(a$ /A-a) -%)0$
".
O // CH3 * C * OH
A-a) E$ana$
A-a) C0ka/A-a) a-%$a$ A-a) )%$ana ka&7k-(la$
3.
A-a) P&+ana$
A-a) +&+(na$ A-a)
4.
O // CH3 * ,CH"" * C * OH
A-a) B0$(&a$/a-a) )%n$%a A-a) ..
O // CH3 * ,CH"3 * C * OH
A-a) Qal%&a$ .........
;.
(ka a-a) ka&7k-(la$ $%&-%70$ )%n(ka$ a7an $%n$0 a&a +%)7%&(an n)& 0&0$ a$) C +a2a &an$a( 2()0la( 2a&( a$) C 00- <0n-(. CH3 ! CH" ! CH" ! CH" ! CH ! COOH
CH3! CH ! CH"! CH" ! COOH
CH3 A-a) "!)%$(l 1%k-ana$ CH3 ! CH ! COOH
CH3 a-a) 4!)%$(l +%n$ana$ CH3! CH ! COOH
OH A-a) "!1(2&k-(l +&+ana$ ,A-a) lak$a$/a-a) -0-0
NH" a-a) "!a)(n +&+ana$ ,A-a) α!a)(n +&+ana$= alan(n%
A-a) ka&7k-(la$ &an$a( +an6an 7(a-a k($a k%nal -%7aa( a-a) l%)ak. A-a) l%)ak an +al(n 7anak $%&2a+a$ 2( ala) 2(an$a&ana a-a) +al)($a$= a-a) -$%a&a$= a-a) l%a$= 2an a-a) l(nl%a$. '(an$a&a a-a)!a-a) l%)ak $%&-%70$ a2a an )%&0+akan a-a) l%)ak 6%n01 2an a2a +0la an )a-(n )%nan20n (ka$an &anka+ +a2a &an$a( a$) C na. A-a) l%)ak 6%n01 :
C ?; H33 COOH : a-a) +al)($a$ C?8 H3; COOH : a-a) -$%a&a$
A-a) l%)ak $ak 6%n01 : C?8H33COOH : a-a) l%a$ ,)%)+0na( ?70a1 C C C?8H3?COOH : a-a) l(nl%a$ ,)%)+0na( " 70a1 C C B(la 00- ka&7k-(lna a2a 20a -%na5a ($0 2(7%&( na)a 2%nan ak1(&an !2(a$. A-a)!a-a) (n( 2a+a$ )%nala)( +l()%&(-a-( )%)7%n$0k -%&a$!-%&a$ -(n$%$(k -%+%&$( n(ln 2an $%$&n. A-a) l0$a)a$ 2(0nakan 0n$0k 7a1an +%)70a$an +%n%2a+ )a-akan a($0 )n -2(0) l0$a)a$ ,MSG.
?" @ P a %
R+#+! St+kt+
R+#+! Molek+l
HOOC ! COOH
,COOH "
HOOC * CH" ! COOH
CH",COOH"
HOOC * ,CH""!COOH
C"H4,COOH "
HOOC * ,CH"3 * COOH
C3H,COOH"
HOOC * ,CH"4 * COOH
C4H,COOH "
Na#a !en3a4a
A-a) %$an2(a$ ,A-a) k-ala$ A-a) . ,A-a) Malna$ A-a) .. ,A-a) S0k-(na$ A-a) ... ,A-a) l0$a)a$ A-a) .. ,A-a) a2(+a$
A-a) <&)a$ a2ala1 a-a) an +al(n k0a$ 2(an$a&a a-a)!a-a) ka&7k-(la$ n&)al 2an -%&(nkal( 2(0nakan 0n$0k )%n0)+alkan la$%k-. '($(n6a0 2a&( -%( 60)la1 +%n0naanna a-a) a-%$a$ a2ala1 a-a) &an(k an +al(n +%n$(n. A-a) (n( )%&0+akan 7a(an 0$a)a 2a&( 0ka= akn( "; 2a&( a-a) a-%$a$ 2ala) a(&. A-a) a-%$a$ an$a&a la(n 2a+a$ 2(+%&l%1 2%nan a&a <%&)%n$a-( $%$%-. Sifat A!a# Ka"ok!ilat:
S(
RCOONa # H"O
CH3COOH # NaOH
CH3COONa # H"O
7. &%ak-( 2%nan H"SO4 2an P"O; )%)7%n$0k an1(2&(2a a-a) O // CH3 ! C ! OH O // CH3 ! C ! OH
.
H"SO4 +%ka$
O // CH3 * C O / CH3 * C O
&%ak-( 2%nan alk1l )%)7%n$0k %-$%& O // R * C * OH # ROH
O // R * C ! OR # H"O
O // CH3 * C * OH # HOCH" ! CH3
O // CH3 * C * O ! CH "CH3 # H"O
2. &%ak-( 2%nan PCl; )%)7%n$0k a-(l 1al(2a O // R ! C ! OH # PCl; O // CH3 ! C ! OH # PCl;
O // R * C ! Cl
# POCl3 # HCl
O // CH3 * C ! Cl
# POCl3 # HCl
5.6. 2. ESTER E-$%&= -ala1 -a$0 2a&( -%na5a &an(k an -ana$ 7%&0na= 2a+a$ 2(07a1 )%n6a2( 7%&an%ka -%na5a la(n. E-$%& 7anak 2(60)+a( 2( ala). L%)ak 2an l(l(n l%7a1 a2ala1 %-$%&. E-$%& 60a 2(0nakan 0n$0k +l()%& -(n$%$(k ,+l(%-$%&= 2a&n. E-$%& a$-(&( )%n%7a7kan a&)a an -%2a+ 2ala) 7anak 70a1 2an +a&<0). C($a&a 70a1 ?3 @ P a %
ala)(a1 )%&0+akan &a)0an &0)($ 7%&)aa)!)aa) %-$%& 7%&-a)a 2%nan -%na5a &an(k an la(n. C($a&a-a 2a&( %-%n-% 7(a-ana 1ana )%&0+akan a)+0&an 2a&( 7%7%&a+a -%na5a %-$%&. B%7%&a+a n$1 %-$%& 7%-%&$a ($a&a-a an 2($()70lkan 2a+a$ an2a 7aa +a2a $a7%l 2(7a5a1 (n(.
Ta"el : -e"ea/a e!te /ilihan "e!eta "a+ 3ang 0iti#"+lkan
Na)a T&(>(al
S$&0k$0&
M%$(l a-%$a$ E$(l a-%$a$ P&+(l a-%$a$ E$(l B0$(&a$ I-a)(l a-%$a$ I-70$(l +&+(na$
CH3CO"CH3 CH3CO"CH"CH3 CH3CO",CH""CH3 CH3,CH""CO"CH"CH3 CH3CO",CH""CH,CH3" CH3CH"O"CH"CH,CH3" CO"CH3
M%$(l -al(-(la$
Ba0 Enak Enak S%+%&$( 70a1 +%a& S%+%&$( n%naS%+%&$( 70a1 +%a& S%+%&$( &0) S%+%&$( an2a+0&a
OH B(la 2(+%&1a$(kan n$1!n$1 +a2a $a7%l 2( a$a- 2a+a$ 2(ka$akan 7a15a %-$%& )%&0+akan $0&0nan a-a) ka&7k-(la$ 2an 2(na$akan 2%nan &0)0- 0)0): R!CO O ! R E-$%& 2a+a$ $%&7%n$0k 7(la a-a) ka&7k-(la$ 2(&%ak-(kan 2%nan alk1l. R%ak-(na 2ala) k%-%$()7an! an -%-0a( 2%nan +%&-a)aan : A-a) ka&7k-(la$ # Alk1l R!CO # OH
HOR
E-$%& # A(& R!CO # H"O O ! R
Ka&%na %-$%& $%&7%n$0k 2a&( &%ak-( an$a&a a-a) ka&7k-(la$ 2%nan alk1l= )aka -%na5a %-$%& 2( 7%&( na)a -%7aa( alk(l ka&7k-(la$ a$a0 a&(l ka&7k-(la$= na)a 00- alk(l a$a0 a&(l an $%&(ka$ +a2a a$) k-(%n 2(an$0)kan -%7aa( +%nan$( ka$a a-a). Cn$1 :
CH3 ! CH" ! C O O ! CH" !CH3
CH3 ! CH ! C O CH3 O ! CH" ! CH3
%$(l +&+ana$
%$(l= "!)%$(l +&+ana$
Un$0k l%7(1 )%n2ala)( -$&0k$0& 2a&( %-$%&= a&(la1 &0)0- -$&0k$0& 2a&( C 4HO" an $(2ak )%nan20n (ka$an &anka+ +a2a &an$a( a$) C na. P%&$a)a kal( an2a $%n$0 akan )%n0l(-kan &0)0-$&0k$0& 2a&( a-a) ka&7k-(la$na= a($0: CH3 ! CH" ! CH" ! C O a-a) 70$ana$ OH '%nan )%)$n -a$0 a$) C an +al(n 060n 2an k%)02(an )%nan$(kana +a2a a$) H an )0nk(n an2a akan )%)+%&l%1 &0)0- -$&0k$0&: CH3 ! CH ! C O 2an CH3 OH a-a) "!)%$(l +&+ana$
CH3 ! CH" ! C O O ! CH3 )%$(l +&+ana$
S%$%&0-na= 2%nan a&a an -a)a an2a akan )%n2a+a$kan &0)0- -$&0k$0& 7%&(k0$: CH3 ! C O
H!C O ?4 @ P a %
O ! CH" ! CH3 %$(l )%$anl 2an
O ! CH" ! CH" ! CH3 n!+&+(l )%$ana$
O // H ! C ! O ! CH ! CH3
Un$0k l%7(1 )%)a1a)( +&-%- +%)7%n$0kan %-$%& lak0kanla1 k%(a$an 7%&(k0$:
CH3 (-+&+(l )%$ana$
Kegiatan /e#"+atan E!te
E-$%& 2a+a$ 2(70a$ 2%nan 6alan )%&%ak-(kan a-a) ka&7k-(la$ 2an alk1l 2%nan ka$al(- H "SO4 +%ka$= )(-alna : CH3COOH # CH3OH
CH3COOCH3 # H"O
&aa Ke7a ?. Pana-kan k(&a!k(&a ? )l a(& 2ala) %la- k()(a "; )l= -a)+a( -010na k(&a!k(&a 8 C. ". S%)%n$a&a a(& 2(+ana-kan: a. )a-0kkan 3 )l %$anl= 3 )l a-a) a-%$a$ +%ka$ 2an " $%$%- a-a) -0l
-ahan 3ang 0i8a#/+kan
Se"el+# 0i/ana!kan
Setelah 0i/ana!kan
?. E$anl # a-a) a-%$a$ # a-a) -0l
. .
. .
". M%$anl # a-a) -al(-(la$ # a-a) -0l
*etan3aan ?. T0l(- +%&-a)aan &%ak-( %$anl 2%nan a-a) a-%$a$ ". A+a <0n-( a(& +a2a $a70n &%ak-( k%(l 3. M%na+a +%)ana-an 1a&0- 2( +%&$a1ankan +a2a -010 C 4. 7%&(kan na)a 7%7%&a+a 7a1an 2(&0)a1)0 an k(&a!k(&a )%nan20n %-$%& ;. B%&(kan na)a %-$%& an 2(70a$ 2ala) k%(a$an (n(
E-$%& 7(a-ana )%)+0na( $($(k l%l%1 2an $($(k 2(2(1 l%7(1 &%n2a1 2a&( +a2a a-a) ka&7k-(la$ an )%)+0na( 60)la1 a$) C -a)a. In( 2(-%7a7kan ka&%na %-$%& $(2ak )%)+0na( 00- 1(2&k-(l 7%7a-. '(-a)+(n 2(k%nal %-$%& 2a&( alk1l )n>al%n-( 60a 2(k%nal %-$%& %-$%& 2a&( alk1l +l(>al%n-(= $%&0$a)a %-$%&!%-$%& 2a&( l(-%&l. E-$%& l(-%&l an +%n$(n 2an l0a- +%n0naanna a2ala1 l%)ak 1%5an( 2an na7a$(.
I-)%& a-a) ka&7k-(la$ 2an %-$%& Ca&(la1 (-)%& C;H?O= -a$0 a$) C 2(0nakan -%7aa( 00- <0n-( a($0 * COOH ,a-a) ka&7k-(la$ a$a0 ! COO * ,%-$%& A-a) ka&7k-(la$ C4H9COOH
E-$%& R * COO * R
A2a 4 (-)%& CH3 * CH" * CH" ! CH" ! COOH CH3 * CH" * CH ! COOH
R n 3
R n ?
a2a " (-)%&
O ?; @ P a %
CH3
CH3
// CH3 ! C O * CH" * CH" * CH3
CH3 * C * COOH
CH3
? @ P a %
O //
CH3
CH3 ! C
CH3 * C * COOH
O * CH * CH3
CH3
CH3 O // CH3 * C * O * CH * CH3
CH3 O // CH3 * C * O * CH" * CH" * CH3 O // CH3 *C * O * C * CH3
CH3
5.6.1 Le#ak 0an #in3ak Banak 2(an$a&a 7a1an an 2(+aka( -%1a&(!1a&( $%&)a-0k lnan l%)ak a$a0 )(nak= a$a0 7%&a-al 2a&( +%nla1anna. Ma&a&(n )(-alna a2ala1 l%)ak an -02a1 )%nala)( +&-%- $%&$%n$0= -%1(na )%)+0na( -(
L%)ak 2an )(nak an $%la1 $%&-()+an la)a= akan -%2(k($ $%&1(2&l(-a. A-a) an $%&6a2( $%&0$a)a a-a) l%)ak $ak 6%n01= $%&k-(2a-( l%1 02a&a )%n1a-(lkan al2%1(2= k%$n 2an a-a)!a-a) an l%7(1 -%2%&1ana an 7%&7a0 $%n(k. Un$0k )%n1(n2a&( +&-%- $%&-%70$ 2(a$a-= )(nak an 7anak )%nan20n a-a)!a-a) $ak 6%n01 ,C C 2(a2(-( 2%nan H " 2an )%n0nakan ka$al(- -%&70k N(. Ha-(l 2a&( 1(2&(na-( )(nak 2(1a-(lkan l%)ak +a2a$ an 7a(a-a 2(-%70$ )a&a&(n a$a0 )%n$%a $(&0an. T%n$0na k5al($a- )a&a&(n an 2(+%&l%1 $%&an$0n +a2a 60)la1 ka2a& a-a) l%)ak an $ak 6%n01 an $%&-(-a 2(2ala)na. Mak(n k%(l ka2a& a-a) l%)ak $ak 6%n01 an $%&-(-a )ak(n 7a(k )0$0 2a&( )a&a&(n $%&-%70$. O // CH" ! O ! C ! C ?8 H3;
O // CH" ! O ! C ! C ?; H3? O
N(
O // // CH ! O ! C ! C?8H3; O // O CH" ! O ! C ! C ?8H33
CH" ! O ! C ! R ?
CH" ! OH
O // CH ! O ! C ! C?8 H3; O // CH" ! O ! C ! C ?8 H3;
l(-%&l $&( O -$%&%a$ a$a0 $&(-$%a&(n // ,l(-%&(2a -%2%&1ana
//
l(-%&l +al)($= -$%a&= l%a$
CH ! O ! C ! R " # 3,l(-%&(2a NaOH a)+0&an CH ! OH
# 3 R * C * O Na
O 2a&( -0a$0 l(-%&(2a 2%nan 7a-a k0a$ ,-0a$0 +&-%-a70n an 2(-%70$ Sa+n(<(ka-( )%n1a-(lkan H(2&l(-( N( // l%)ak ,-a70n a&a) a-a) l(-%&l 7%7a-. Ol%1 ka&%na ($0,+&%ak-(na 2(-%70$ &%ak-( +%na70nan $&(l%(n 2an ,l # 3H $&(-$%a&(n " CH ! O ! C ! R CH ! OH ,-a+n(<(ka-(. " 3 " l(-%&l O O // CH" ! O ! C ! C?; H3?
// CH" ! O ! C ! C?8 H3;
S(
,C?8H3;COO"Ca,- # "Na#
Ka&%na )%)7%n$0k %n2a+an -a70n $ak 2a+a$/-0ka& 7%&70(1= -%1(na a(& -a2a1 $(2ak 7a(k 0n$0k )%n0( ,%n2a+an akan )%n$&( +aka(an . 3. Sa70n an 0)0) 2(0nakan a2ala1 -a70n Na= -%2an -a70n K 0n$0k k%+%&l0an k10-0-. Soal Latihan
?. T0l(-kan na)a -%na5a!-%na5a 7%&(k0$: a. CH3 ! CH" ! COOH 7. CH3 ! CH" ! COOCH3 . CH3 ! CH" *CH,CH3 ! COOH 2. CH3 !CH ! C O CH3 CH3 O ! CH" ! CH ! CH3 %. CH3 * CH ! C O CH3 O ! CH" ! CH3 ". T0l(-kan &0)0- -$&0k$0& 2a&( -%na5a!-%na5a 7%&(k0$: a. A-a) !"!)%$(l 70$ana$ 7. A-a) ! "!%$(l 70$ana$ . E$(l= "!)%$(l 70$ana$ 2. T%&-(%& 70$(l +&+ana$ %. I-+&+(l %$ana$ ? @ P a %
3. T%n$0kan (-)%&!(-)%& 2a&( -%na5a an )%)+0na( &0)0- )l%k0l C;H?O" -%&$a na)a 2a&( -%na5a 7%&-ank0$an. 4. S%70$kan %)+a$ k%0naan %-$%& 2ala) k%1(20+an -%1a&(!1a&(. ;. S%70$kan " +%&7%2aan an$a&a )(nak 2an l%)ak . Baa()ana a&a )%n07a1 a-a) l%)ak $(2ak 6%n01 )%n6a2( a-a) l%)ak 6%n01 T0l(-kan n$1 &%ak-(na.
5.(.1 HALOALKANA '%nan 7%&k%)7anna (l)0 +%n%$a10an 2an $%knl(= k%70$01an 1(20+ )an0-(a 2(7an$0 l%1 7%&7aa( 7a1an -(n$%-(-= -%+%&$( +la-$(k= $%k$(l= +%la&0$= ka&%$ -(n$%-(-= (n-%k$(-(2a 2an 7a$!7a$an. Ba1an * 7a1an $%&-%70$ 2(70a$ 2a&( 7%&7aa( a$ k()(a= 2(an$a&ana 1alalkana. Halalkana 2a+a$ 2(ana+ -%7aa( $0&0nan alkana 2%nan -a$0 a$a0 l%7(1 a$) H 2a&( alkana 2(an$( 1al%n. Halalkana an -%&(n 2(60)+a( 2ala) la7&a$&(0) )(-alna ka&7n $%$&a kl&(2a ,CCl 4 -%7aa( +%la&0$= Kl& <&) ,CHCl 3 -%7aa( 7a$ 7(0-. S%7aa( +%la&0$ ,T(++ E 2(0nakan -%na5a ?=?=? $&(kl&%$ana. Hal alkana an 7anak 2(0nakan 0n$0k 7a1an +%n2(n(n +a2a <&%%%& 2an -%7aa( a%&-l $%$a+( 2(-&$( )a-a&aka$ In$%&na$(nal ka&%na )%n%7a7kan +%n%)a&an 02a&a a2ala1 CFC ,C1l& Fl0& Ca&7n. Pa2a 7a7 (n( akan 2(7a1a- &%ak-( +%)70a$an 1alalkana= k%0naan 2an 2a)+ak n%a$(
5.(.2. Reak!i /e#"+atan haloalkana Pa2a 0)0)na 1alalkana 2a+a$ 2(+%&l%1 2a&( &%ak-( -07$($0-( alkana ,a- ala) ,LNG a$a0 LPG 2%nan 1al%n 2%nan 7an$0an -(na& )a$a1a&( ,-(na& 0l$&a >(l%$. R%ak-( alkana 2%nan
-. 0. >.
CH3Cl # Cl",
-. 0.>.
CH"Cl" # Cl",
-. 0. >.
CH3Cl
CH3Cl,
-. 0. >.
# Cl",
#
HCl,
CH"Cl",l #
HCl,
CHCl3,l
#
HCl,
CCl4,l
#
HCl,
Halalkana 60a 2a+a$ 2(+%&l%1 2a&( 7%7%&a+a &%ak-( 2(7a5a1 (n(: ?.
ROH # PD3 → RD # P,OH 3 CH3!CH"OH # PCl3 → ..
".
ROH # HD → RD # H"O CH3!CH"OH # H"O
3.
# .
→ .. # .
CnH"n # HD → RD CH" CH" # HCl → ..
;.3.3
Tatana#a haloalkana
Ta$ana)a +a2a 1alalkana -a)a -%+%&$( na)a -%na5a ka&7n la(nna= a($0 7%&2a-a&kan &an$a( alk(l 2an 1al%n an $%&(ka$ +a2a a$) C!na. ?. P%)7%&(an n)& 0&0$ -%2%)(k(an -%1(na C an )%n(ka$ 1al%n )%n2a+a$ n)& $%&k%(l. ". (ka 60)la1 a$) 1al%n l%7(1 2a&( ? 2(7%&( a5alan 2(= $&(= $%$&a 2-$. Cn$1 : H
H
H * C * Cl
H * C * Cl
H Kl& )%$ana
Cl 2(kl&)%$ana
B%&( na)a!na)a -%na5a 7%&(k0$: F H H
F * C * Cl
H * C * C * Cl
H
Cl
H * C * C * Cl
H Cl ?=?=? $&(kl&)%$ana
H
CH3
H * C * C * CH 3
?9 @ P a %
Cl
Cl H
.
CH3 * CH * CH3
Cl
.
CH3 * CH * CH,CH 3"
B&
11.2.1
H
Cl
H
/ CC / H H .
Cl ..
-e"ea/a eak!i haloalkana RD # AOH → ROH # AD
CH3 * CH,Cl * CH 3 # AOH
→
..
# .
RD # " Na → R * R # " NaD CH3 * CH,Cl * CH 3 # " Na RD # NH 3 →
→ # .
RNH" # HD
CH3 * CH"Cl # NH 3 →
. #
RD # M → RMD CH3 * CH"Cl # M → RD # ACN →
..
RCN # AD
CH3 * CH * CH3 # ACN →
# .
B&
5.(.'. Keg+naan !en3a4a haloalkana 0an 0a#/akn3a teha0a/ lingk+ngan. K%0naan -%na5a 1alalkana 2ala) k%1(20+an -%1a&(!1a&( -ana$ l0a-= )(-alna -%na5a &ankl& 7anak 2(0nakan -%7aa( (n-%k$(-(2a ,''T= BHC= Ban= +%la&0$ ,CCl 4= CH3!CCl3= +%n2(n(n=a%&-l ,CF "Cl"= +la-$(k -%+%&$( T%(l%$ an )%n060 70)(. K%l%7(1an -(na& 0l$&a >(l%$ an )%na+a( 70)( 2a+a$ )%n%7a7kan +%nak($ kank%& k0l($. 7. Banak -%na5a &an kl& an 2(0nakan -%7aa( +%-$(-(2a -0ka& $%&0&a( -%1(na 2a)+ak an 2($()70lkan -ana$ l0a- 2an )%&0-ak l(nk0nan. S%7aa( n$1 +%n0naan ''T= al2&(n an -0ka& $%&0&a( 2(-a)+(n 2a+a$ )%)70n01 7(7($ +%nak($ +a2a $ana)an 60a 2a+a$ )%)70n01 1%5an!1%5an a(& 2an 1%5an!1%5an +%)akan 7anka(= -%7a(an la( $%&(-a+ l%1 $0)701!$0)701an 2an )a-0k k% 2ala) $0701 )an0-(a. . Halalkana -%7a(an 7%-a& -%7aa( 7a1an 2a-a& +%)70a$an +la-$(k an -0ka& 2(0&a(kan l%1 )(k&&an(-)%= -%1(na +%)aka(an +la-$(k 2ala) k%1(20+an -%1a&(!1a&( )%n()70lkan 2a)+ak $%&1a2a+ l(nk0nan $%&0$a)a +%n%)a&an $ana1. P%)7aka&an -a)+a1 +la-$(k 60a akan )%n()70lkan +%n%)a&an 02a&a. 2. I2<&) ,CHI3 an +%&na1 2(0nakan -%7aa( 7a$ l0ka 7%&7a0 $(2ak %nak 2an 7%&a0n %. Kl&<&) ,CHCl3 -0a$0 a$ a(& $(2ak 7%&5a&na 2an 7%&7a0 -%2a+ 2an 7%&-(
?. 7%&(kan $(a n$1 -%na5a 1alalkana an -%&(n an2a 60)+a( 2ala) k%1(20+an -%1a&(!1a&( ". T0l(-kan &%ak-( -07$($0-( 1al%n +a2a )%$ana -a)+a( $%&7%n$0k CCl 4. 3. CFC a$a0 <&%n )%)+0na( &0)0- 2an na)a -%-0a( 2%nan $a$ana)ana. " @ P a %
a. $0l(-kan &0)0- 2an $a$ana)ana. 7. S%70$kan " k%0naan CFC 2ala) k%1(20+an -%1a&(!1a&( . Baa()ana a&a )%nan0lan( +%n%)a&an ak(7a$ +%n0naan CFC. 4. T0l(-kan 3 &%ak-( -(n$%-(- an )%n0nakan 7a1an 2a-a& 1alalkana.
IDENTIFIKASI SENYAWA KARBON Rumus Gugus Fungsi Ciri-ciri Umum 1 R!"#si $#si%"si dengan KMnO4, K 2Cr2O7. A&#$'$& (rim!r ) "&%!'i% )"s"m #"r*$#si&" A&#$'$& s!#un%!r ) #!$n A&#$'$& !rsi!r ) i%"# *is" %i$#si%"si 2 R!"#si %!ng"n &$g"m N",K R-OH + N" .RON" + H 2 / Reaksi dengan HX, PCl 3 ata PC!. R-OH " HX # RX " H2O Alkohol / -OH R-OH " PC!3 $ R-Cl " H 3PO3 R-OH " PCl% # RCl " POCl3 " HC! 0 R!"#si %!ng"n "s"m #"r*$#si&" R-OH + RCOOH . RCOOR !s!r, H"rum3 + H2O 4 Reaksi dengan asa& sl'at R-OH " H 2(O, )ada CnH2n+2O sh *3+C $ eter. Pada titik didihna tinggi *+oC0 5 Tii# %i%i' inggi ?. Reaksi oksidasi R-O-R " O2 # CO2 " H2O 2 R!"#si %!ng"n &$g"m N",K R-O-R + N",K ) "# *!r!"#si 3. Reaksi dengan HX, PC! 3, ata PC!% R-O-R " HX # R-OH " RX (R panjang menjadi alcohol, R pendek menjadi alkil halide) 1ter / -OR-O-R " PC!3 # tak ereaksi R-O-R "PCl% # R-Cl " R-Cl " POC!3 4. Reaksi dengan asa& karoksilat R-O-R " RCOOH # tak ereaksi 4 Tii# %i%i' r!n%"' A&%!'i% , U6i F!'&ing , B!n!%ic Menghasilkan C 2O enda)an -CHO &erah ata0 dan asa& karoksilat. U6i T$&&!ns / 7!r"# "m$ni"#"& Menghasilkan Ag 5er&in )erak0 dan Asa& karoksilat. CnH2nO Di$#si%"si direaksikan dengan KMnO 4, K 2Cr2O70 &enghasilkan asa& karoksilat. K!$n , -COTi%"# *!r!"#si %!ng"n U6i F!'&ing , T$&&!ns, %i$#si%"si As"m - B!rsi8" "s"m K"r*$#si&" , - B!r!"#si %!ng"n "&#$'$& ) m!ng'"si&#"n !s!r -COOH - Di'i%r$&isis ) !"( CnH2nO2 Es!r , -COO- B!rsi8" n!r"& - T"# *!r!"#si %!ng"n "&#$'$& - Di'i%r$&isis ) m!ng'"si&#"n "&#$'$& %"n "s"m #"r*$#si&" REAKSI U9I SENYAWA KARBON :AIN 1 U6i I#""n R"ng#"( U6i R!"#si
Ciri 8ika 9arna 5oklat ro& Adana ikatan CH3CH6CH2 " r2 # CH3-CHr'i&"ng erarti ada rangka) # Br$min"si CH2r ikatan rangka) :etak ikatan rangka) CH26CH-CH3 " O3 # CH3OH " HO- Hasil # O;$nis"si CH2CH3 &etanol *C0 + Metanol etanol2C0 etanol Kesi&)lan rantai ta&a 6 *"2 6 3 , sehingga "? @ P a %
(ena9a asal 6 *)ro)ena OH I
O II
2 U6i I$%$8$rm CHI/3 (ena9a alkohol, aldehid, dan keton ang &engikat &etil di seelah -OH R- CH - CH 3 0 ata R- C - CH 3 0 da)at ereaksi dengan )ereaksi iodo'or& ! 2 dala& ;aOH0 &enghasilkan kristal kning iodo'or& CH! 30. Contoh sena9a etanol, etanal, aseton, 2)ro)anol, 2- tanol, dan 2- tanon. R-CO-CH3 # CH!3 " R-COO;a enda)an kning0
KEGUNAAN SENYAWA KARBON <gs =ngsi Alkohol /Alkanol / CnH2n"2O/ -OH
;a&a (ena9a Metanol CH3OH0
-
1tanol C2H%OH0
*,2 1tanadiol/ 1tilenglikol *,2,3 )ro)anatriol / gliserol 1ter/ Alkoksi alkana/ CnH2n"2O/ -O-
Aldehid/ Alkanal/ CnH2nO/ -CHO
@ietil eter/ 1ter C4H*+O0 Metil tersier til eter MB10 Metanal HCHO0
1tanal/ Asetaldehida/ CH3CHO Keton/ Alkanon/ CnH2nO/ -CO-
Asa& Karoksilat/ Asa& alkanoat/ CnH2nO2/ -COOH
Pro)anon/ Aseton
tanon Asa& &etanoat/ Asa& =or&at/ HCOOH Asa& 1tanoat/ Asa& Asetat/ Asa& Cka/
-
Kegnaan >ntk )e&atan ))k, oat, )lastik, dan sena9a organik lain se)erti ester. seagai )elart le&ak ata sena9a organik lain. Mer)akan 5a&)ran ahan akar ensin. (eagai ?at denatrasi etanol (eagai )elart (eagai &in&an eralkohol. oat tonik& ?at 9arna )ar'& serat sintetis ahan akar alternati' @esin'ektan/ antise)tik/ )e&nh k&an at anti ek )ada radiator/ )endingin (eagai )elart (eagai ahan ak serat dakron. ahan oat atk )ele&a )ada losion ahan ta&ahan dala& oat-oatan ahan )eledak. (eagai )elart sena9a-sena9a organik (eagai oat is anastesi0 (eagai ?at aditi' )ada ensin
- ahan =or&alin 4+-4% &etanal dala& air0 seagai desin'ektan dan )enga9et s)esi&en iologi/ &aat. - (eagai ahan )lastik )oli &etanal. - (eagai )elart - ahan )e&atan asa& karoksilat - seagai ?at 9arna, - ahan )e&at )lastik, - ahan )e&at karet sintetis. - (eagai ahan ak sena9a ester/ )lastik Pers)eD - (eagai )elart )lastik - Pe&ersih 5at kk. - (eagai )elart - ahan ak tekstil - Mengg&)alkan getah karet :ateks0
- & &asakan - Min&an erkhasiat - (eagai ahan serat raon "" @ P a %
<gs =ngsi
;a&a (ena9a CH3COOH Asa& Pal&itat dan Asa& (tearat Asa& oksalat Asa& tartrat Asa& adi)at
1ster/ Alkil Alkanoat/ CnH2nO2/ -COO-
Kegnaan - ahan serat sintesis dan )lastik , - ?at )engasa& &akanan. - (eagai ahan dasar san
- &enghilangkan karat - )e&atan ?at 9arna. - seagai ?at )engasa& &in&an, )er&en, dan aking )o9der. - ahan &e&at nilon. - (eagai ahan dasar san - (eagai aro&a essen5e0 eragai )rodk &akanan - ahan ak )oliester kain0 - (eagai )elart - Kegnaan dala& entk lilin di antarana seagai &ala& ntk &e&atik - @ala& entk le&ak/&inak dignakan ntk &e&at san dan ahan &akanan &argarin0
"3 @ P a %
