1
CHEM 2425
Unit 19 Homework
1. Name the following compounds.
COOH
(a)
Br
(b) CH3CH=CHCHBrCO2H
(c) HO2CCH2CH2CO2H
Cl
(d)
HO2C
CH3
CH CH CH2 CH CO 2H
CH2CH3
(e) HCO2H
2. Put the following lists of compounds in order of increasing acidity.
(a) CH3CH2CO2H
CH3CO2H
(CH3)3CCO2H
(CH3)2CHCO2H
COOH
COOH
COOH
(b)
Cl
O 2N
CH3
(c) CF3CO2H
FCH2CO2H
F2CHCO2H
3. Show the mechanisms for the following reactions.
O
O
O
(a)
OH
OHΔ
COOH
2
CO 2H
HO2C
CO 2H
Δ
(b)
4. Show the products of the following transformation. If no reaction occurs, write “no rxn”.
(a) PhCHO + KMnO4 _____>
H2SO 4
(b) PhCH2OH + K2Cr2O7
CH3
KMnO4
(c)
Δ
CH3
(d)
C(CH3)3
(CH3)2CHCN + H3O+
Δ
O
C
(e)
CH3
(f) (CH3)2CHMgBr + CO 2
(g) (CH3)2CHCO2H + LiAlH4
(h) PhCO2H + KMnO4 _____>
(i) (CH3)2CHCO 2H
(j)
+ Cl2
CH3COCH2CO 2H
xs I2, OH(2) H3O+
(2) H3O+
_____
>
cat. P
Δ
5. Show the reagents necessary to accomplish the following transformations.
(a) CH3CH2CHO ___________________________________________> CH3CH2CO2H
(b) CH3CH2CHO ___________________________________________> CH3CH2CO2H (second method)
(c) PhCH2OH _______________________________________________> PhCO2H
(d) PhCH3 ______________________________________________________> PhCO2H
OH
(e)
CH3
CHCN
OH
CH3
CHCOOH
3
CH3
CH3
(f)
Br
HO2C
(g) PhCO2H ___________________________________________________> PhCH2OH
(h) PhCH2CH2CO2H ___________________________________________> PhCH2CHBrCO2H
O
HO
CN
(i)
___________________________________________
(j) PhCOCH2CO2H
>
PhCOCH3
6. Show how to perform the following procedures using multi-step syntheses.
(a) CH3CH2CHO
→
CH3CH2CHOHCO2H
(b) PhCH2CO2H
→
PhCH(NH2)CO2H
(c) CH3CO2H
→
HO2CCH2CO2H
(d) CH3CH2CH2Br →
CH3CH2CH2CH2CO2H
7. Show how PhCH2CO2H can be prepared by starting with bromobenzene and any other needed
organic and inorganic reagents.
8. Fill in the structures for the intermediates and products (A-G) in the following synthetic
scheme.
CH3
LiAlH4
CH
CH3
CO 2H
(2)
H3O+
PBr3
A
Mg
B
C
Et2O
CO 2
(2) H3O+
G (C6H10O4)
H3O+
Δ
F
NaCN
E
Cl2
cat. P
D
9. The IR spectra in Figures 1 and 2 correspond to 2 of the following 4 compounds. Determine
which spectra go with which compounds.
4
HO
COOH
CH2COOH
CH3
CH COOH
CH CHCOOH
10. Figures 3-5 are NMR spectra of carboxylic acids. Determine the structure of these acids from
the information given.