ลาดับที่......................
2302169 Chem Med Studt
ก า ร บ้ า น ค รั ้ ง ที่ 2 Aldehyde, Ketone, Carboxylic Acid and Derivatives
P a g e |1
ชื่อ-สกุล.....................................................................................คณะ.............................................เลขประจำตัวนิสติ .............................
ส่งการบ้านที่กล่องรับ หน้ าห้อง 1326/7 ชัน้ 13 อาคารมหามกุฏ ภายในวันที่................................................
1) Give the IUPAC name for each compound.
1.1
(CH 3) 3CCH2 CHO
O
1.2
Cl
O
1.3
1.4
(H3 C)2 HC
CH 3
O
1.5
PhH2 C
OHC
O
1.6
2) Draw the product formed when phenylacetaldehyde (C6H5CH2CHO) is treated with each reagent.
2.1 NaBH4, CH3OH
2.4 Ph3P=CHCH3
2.2 [1] LiAlH4; [2] H2O
2.5 (CH3CH2)2NH, mild acid
2.3 [1] CH3MgBr; [2] H2O
2.6 HOCH2CH2OH, H+
2302169 Chem Med Studt
ก า ร บ้ า น ค รั ้ ง ที่ 2 Aldehyde, Ketone, Carboxylic Acid and Derivatives
P a g e |2
3) Draw the products formed in each reaction sequence.
3.1
[1] Ph 3P
CH 3CH2 Cl
3.2
[2] BuLi
[3] (CH 3 )2 C=O
CH 2Br
CH 2 Cl
3.3
[1] Ph 3P
[2] BuLi
[3] C 6 H5 CH 2 CH 2CHO
[1] Ph 3P
[2] BuLi
[3] CH 3CH2 CH2 CHO
4) Draw all stereoisomers formed in each reaction.
4.1
Ph3 PH=CHCH2 CH 2CH 3
butanal
4.2
2-butanone
NaCN
HCl
4.3
NaBH4
O
CH 3OH
CH2 CH 3
O
4.4
OH
CH 3OH
HCl
OH
2302169 Chem Med Studt
ก า ร บ้ า น ค รั ้ ง ที่ 2 Aldehyde, Ketone, Carboxylic Acid and Derivatives
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5) Draw the products of each reaction.
5.1
CH 3CH 2CHO
5.2
O
+
H 2N
mild
acid
HOCH 2CH 2OH
H+
5.3
H3 O+
N
HO CN
H3 O+
5.4
heat
5.5
N
H3 O+
6) Show two different methods to carry out each transformation: a one-step method using a Wittig reagent
and a two-step method using a Grignard reagent.
6.1
6.2
cyclohexanone
cyclohexanecarbaldehyde
2302169 Chem Med Studt
ก า ร บ้ า น ค รั ้ ง ที่ 2 Aldehyde, Ketone, Carboxylic Acid and Derivatives
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7) Give an IUPAC name for each compound.
7.1
(CH 3) 2CHCH 2CH 2COOH
7.2
BrCH 2COOH
O
7.3
OH
7.4
CH 3CH 2CH2 COO- Li+
7.5
H 3CH2 C
7.6
COOH
COOH
8) Draw the organic products formed in each reaction.
CrO3
OH
8.1
H2 SO4 , H2 O
8.2 (CH 3) 2CH
CH 3
8.3 CH 3(CH 2) 6CH 2OH
KMnO4
Na 2Cr 2O7
H2 SO4 , H2 O
9) Rank the compounds in each group in order of increasing acidity.
Cl
9.1
Br
COOH
COOH
b
a
COOH
9.2
H3 C
COOH
c
COOH
COOH
F3 C
a
b
c
2302169 Chem Med Studt
ก า ร บ้ า น ค รั ้ ง ที่ 2 Aldehyde, Ketone, Carboxylic Acid and Derivatives
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10) Give an IUPAC name for each compound.
10.1
(CH3 )3 CCOCl
O
10.2
O
10.3 (CH3 )3 CCOOCH 2CH(CH3 )2
O
O
O
10.4
COCl
10.5
Br
10.6
NHCOC 6 H5
11) Rank the compounds in each group in order of increasing reactivity in nucleophilic acyl substitution.
11.1
CH3 CH2 CH 2CONH 2
a
11.2
11.3
CH3 CH2 CH 2COCl
b
CH3 CH2 CH 2COOCH 2CH 2CH3
c
(CH3 CH2 CO)2 O
(CF3CO) 2O
a
b
c
CH 3COOH
CH 3COSH
CH 3COCl
c
a
b
CH3 CH2 CO 2CH2 CH2 CH 3
12) Draw the product formed when pentanoyl chloride (CH3CH2CH2CH2COCl) is treated with each reagent.
12.1 H2O, pyridine
12.4 NH3 (excess)
12.2 ethanol, pyridine
12.5 (CH3CH2)2NH (excess)
12.3 CH3COO-
12.6 C6H5NH2 (excess)
2302169 Chem Med Studt
ก า ร บ้ า น ค รั ้ ง ที่ 2 Aldehyde, Ketone, Carboxylic Acid and Derivatives
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13) Draw the product formed when pentanoic anhydride [(CH3CH2CH2CH2CO)2O] is treated with each
reagent. With some reagents, no reaction occurs.
13.1 SOCl2
13.4 NaCl
13.2 H2O
13.5 (CH3CH2)2NH (excess)
13.3 methanol
13.6 CH3CH2NH2 (excess)
14) Devise a synthesis of each compound using 1-bromobutane (CH3CH2CH2CH2Br) as the only organic
starting material. You may use any other inorganic reagents.
H
N
14.1
O
O
14.2
O
14.3
O