TUGAS KIMIA, FESSENDEN JILID 2, HAL 51 NO. 11.31 ; 11.39 ; 11.40 ; 11.41 ; 11.45 ; 11.47 ; 11.49 ; 11.59
11.31. Tuliskan rumus untuk : (a). bromoaseton, gas air mata yang pernah digunakan sebagai gas perang. (b). biasetil (2,3-butanadion), yang digunakan dalam margarin agar berbau mentega. (c). 4-(4-hidroksifenil)-2-butanon, yang memberikan citarasa buah frambos (raspberry) (d). geranial, ( E )-3, )-3, 7-dimetil-2,6-oktadienal, yang terdapat dalam minyak sereh dan digunakan dalam parfum dan penyadap.
11.39. Ramalkan produk organik utamanya:
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(A)
O
(1)) CH (1 CH3Mgl (2) H+ H+,H ,H2O
CO2H (1) C6H5MgBr
(B)
O
(2)) H+ (2 H+,H2O
Mgl
(1)
(C)
HCHO (2) H+ H+,,H2O
11.40. Sarankan suatu sintesis untuk masing-masing masing-masing senyawa berikut, yang diawali dengan dengan iodometana dan reagensia yang sesuai : (a) 3-metil-3-pentanol; (b) etanol; (c) 2-pentanol.
11.41. Tulislah persamaan untuk sintesis Grignard alkohol berikut ini. Berilah semua jawaban benar yang mungkin.
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(A)
CH2CH2CH2OH
OH (B)
C CH3
11.45. Ramalkan produk organiknya:
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O H2 , katalis tembaga kromit
(A)
150 derajat, 35 atm
OH CHO (B)
(1) NaBH4, CH3CH 2OH
HO
(2)) H2O,H (2 ,H+ +
(C)
NH 2NH 2, KOH, H 2O (HOC OCH H2CH 2)2O, 240 240 der eraaja jatt
O
CH3O (D)
Zn(Hg), HCl pekat
HO
CHO Vanilin
Kalor
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O (E)
CH3CCH3 + NH3
H2, Pt
O (F)
H2, Pt
CH3CCH3 + HOCH2CH2NH2
CH2CH2CH 2NH2 (G)
H2, Pt
O 11.47. Bagaimana melaksanakan pengubahan berikut ini dengan reaksi Wittig? (Mulailah dengan halida organik).
(A)
O
CHCH
CH 2 O
CHO (B) CHO
CH
CHCC CH CCH H 2OC OCH H3
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O (C )
C C H3
C H3 O
C H3 O
C
C H O C 3H
C H3
( D ) ( C H3 2) C
( C H3 2) C
O
C F2
11.49. Senyawa mana berikut ini yang akan memberikan uji Tollens positif?
(A)
CH3CHO
O (B) CH3CCH3
(C)
(D)
O OH
O OCH3
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CH3 H2SO4
(A)
OH
Hangat
O (B)
+ (C6H5)3P
(C)
O
(1) NaC
CH2
CCH3
(2) H 2O, H+
O O (D)
C H3 O2C
SCH2CCH
N
CH2 + O
-
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CH3O
OCH3 H2SO4
(E)
H2O
O (F)
(G)
OLi (1) C6H5CHCH2Li, THF
CH3CH2CH
trans-CH3CH
(2) H2O,
H
CHCO2CH3 + BrCl
CH3 (H)
HCl
CH2Cl 2
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o
150 derajat = 150
