Documentos de Académico
Documentos de Profesional
Documentos de Cultura
-----> CH
3
CH
2
CHCH
2
+ Br
| |
I Br
e)
CH2
H3O
+ H2O ---------->
CH3 HO
f)
H3O (trace)
------------------->
CH2
CH3
4.1 Which of the following reactions is stereospecific? Explain.
4.2 Find and label nucleophiles, electrophiles and bases in the following reactions. Note that
all of the nucleophiles are Lewis bases, so put the label base only if the base does not
perform the nucleophilic function.
4.2
SOLUTIONS TO SAMPLE PROBLEMS:
1.1 Predict the major organic product or products of each of the following reactions.
1.1
1.2 The products are:
a)
O3 Zn
----> ------>
H2O
O
CHO
O O
| | | |
+ HCCH2CH
1.3 The unknowns are:
a) CH3CH2CH=C(CH3)2
b) CHCH2CH3
2. Propose a synthesis of each of these compounds, from the given starting material and any
needed inorganic reagent and/or solvent.
OR this could be accomplished using BH
3
-THF, then H
2
O
2
, OH
-
, no RAR.
2.
3. Mechanisms. Note that balanced equations are used throughout.
OH
a)
H3O
+ H2O ---------->
OH
O
OH2
+ H3O ----->
OH
O
+ H2O
O H
O H + H2O ----->
OH2
OH
+ H2O ----->
OH
OH
+ H3O
b) (CH
3
)
2
CHCH=CH
2
+ HCl -----> (CH
3
)
2
CClCH
2
CH
3
(CH3)2CHCH=CH2 + HCl -----> (CH3)2CHCHCH3 + Cl
H
|
(CH3)2CCHCH3 -----> (CH3)2CCH2CH3
(CH3)2CCH2CH3 + Cl -----> (CH3)2CClCH2CH3
3.
c)
H3O
+ H2O ---------->
CH=CH2
OH
CH2CH3
----->
CH=CH2
OH2
+ H3O ----->
CHCH3
+ H2O
CHCH3 CH2CH3
CH2CH3
+ H2O
----->
CH2CH3
OH OH2
CH2CH3
+ H2O
----->
CH2CH3
+ H3O
H
d) CH
3
CH
2
CH=CH
2
+ Br
2
+ I
-----> CH
3
CH
2
CHCH
2
+ Br
| |
I Br
Br
I
CH3CH2CH=CH2 + BrBr -----> CH3CH2CHCH2
+ Br
CH3CH2CHCH2
Br
+ I
CH3CH2CHCH2 ----->
Br
e)
CH2
H3O
+ H2O ---------->
CH3 HO
CH2
+ H2O
CH3 HO
+ H3O ---------->
CH3
+ H2O
CH3
------>
OH2 H3C
OH2
H3C
+ H2O ------> + H3O
3.
f)
H3O (trace)
------------------->
CH2
CH3
+ H2O
CH2
CH3
+ H3O ----->
CH3
+ H2O
CH3
-----> + H3O
H
4.1. Reaction b) is stereospecific because the two hydrogens are added to the same face of the
alkene in so called syn fashion. As a result, only the cis pair of enantiomers of the product forms.
No diastereomeric trans enantiomers will be found in the product mixture. Reaction a) is not
stereospecific because the carbocation that forms and then rearranges is trigonal planar (note sp
2
-
hybridization of the carbon) and can be attacked from both sides. As a result, both possible
enantiomers will form in approximately equal amounts, so the product will be racemic.
4.2.
Name _____________________________ Ninth Drill Test (Sample A)
Organic Chemistry 2210DR Answer All Questions
1. Predict the major organic product or products the following reactions. Show correct
stereochemisrtry where appropriate. Also label regioselective and stereospecific
reactions.
2. Propose a synthesis of each of the following compounds from the given starting material
and any needed inorganic reagents or solvents.
3. Propose a mechanism for each of the reactions shown.
4. Give the structure of the unknown from the information given.
Name _________________________________________ Ninth Drill Test (Sample B)
Organic Chemistry 2210DR Answer All Questions
1. Predict the major organic product of each of the following reactions.
2. Propose a synthesis of each. You may use any needed inorganic reagents and solvents.
a) (CH
3
)
3
CCl from (CH
3
)
3
COH
b) trans-1,2-cyclohexanediol from bromocyclohexane
3. Propose a mechanism for each of the reactions shown. For problem a), first complete the
equation by predicting the product.
4. Give the structure of the unknown from the information given.