CHM 2210. Organic Chemistry I. Final Exam Review Questions. Examples of the
types of questions you can expect to see on the final ...
CHM 2210 Organic Chemistry I
Final Exam Review Questions Examples of the types of questions you can expect to see on the final
1.
The IUPAC name for the formula CH3CH2CH2CHOHCH=CH2 is 1. 2. 5.
2.
5-hexene-3-ol 1-hexene-5-ol allyl n-butyl ether
2. 4.
1-hexene-3-ol n-propyl ally alcohol
What is the order of reactivity toward SN2 displacement in the following series? A.
C.
B. CH3
Cl
CH3 CH2 CH2 CH2 Cl
CH3 CH2 C CH3
CH3 CH2 CH CH3
Cl
1. 3. 5. 3.
A>B>C B>A>C C>A>B
2. 4.
A>C>B B>C>A
The principal organic product formed in the reaction below is CH2 =CH(CH2 )8 COOH + HBr
peroxide
1.
CH3CHBr(CH2)8COOH
2.
CH2BrCH2(CH2)8COOH
3.
CH2=CH(CH2)8COBr
4.
CH2=CH(CH2)7CHBrCOOH
5.
none of these CH3
4.
Treatment of
with HCl gives
CH3 C CH2 OH CH3
1. CH3 CH2 CH2 CH2 CH2 Cl
2.
CH3 CH2 CH CH2 Cl
CH3
3.
CH3 CH2 C CH3 Cl
5.
CH3 CH3 CH CH2 CH2 Cl
CH3
CH3
4.
CH3 CH CH3
5.
A compound which is insoluble in cold, concentrated sulfuric acid is 1. 3. 5.
6.
sodium tert-butoxide in chloroform hydrogen peroxide and aqueous acetic acetic acid ozone and moist zinc dust periodic acid cold dilute potassium permanganate
the product will be optically active, but have the opposite configuration the reaction will involve racemation a carbanion is formed as an intermediate the rate of the reaction is a function of the concentration of the nucleophile the attacking group will be a strong electrophile
Which does NOT involve a carbocation? 1. 2. 3. 4.
9.
1-hexene ethyl acetate
Which statement is correct for an SN1 reaction at a chiral carbon atom? 1. 2. 3. 4. 5.
8.
2. 4.
Which reagent would convert cyclohexene into a cis-glycol? 1. 2. 3. 4. 5.
7.
n-hexane 2-hexyne benzyl alcohol
(CH3)3CCl + AgNO3 → (CH3)3COH + HCl → (CH3)3CH + Cl2 uv light → CH3CH=CHCH2OH + H3O+ →
The reagent which would distinguish between 1-hexyne and 1-hexene is 1. 3. 5.
Ag(NH3)2+ Br2 in CCl4 NaOH
2. 4.
KMnO4 H2SO4
10. In methyl alcohol solution, bromine reacts with ethylene (ethene) to yield BrCH2CH2OCH3 in addition to 1,2-dibromoethane because 1. 2. 3. 4. 5.
the methyl alcohol solvates the bromine. the ion formed initially may react with Br1- or CH3OH. this is a free radical reaction. the reaction follows Markovnikov’s rule. of none of these reasons.
11. The important minor product from the reaction of sodium cyanide with 2-iodopentane in anhydrous acetone is 1. 3. 5.
1-pentene pentane 4,5-dimethyloctane
2. 4.
2-pentene 2-pentanol
12. The monochloroisomer that predominates in the mixture resulting from the free radical chlorination of CH3CH2CH2CH=CH2 is 1. 3. 5.
ClCH2CH2CH2CH=CH2 CH3CH2CHClCH=CH2 CH3CH2CH2CH=CHCl
2. 4.
CH3CHClCH2CH=CH2 CH3CH2CH2CCl=CH2
13. When a solid organic compound is recrystallized, the cold filtrate from the cooled mixture is 1. 3. 5.
saturated with the compound. 2. entirely free of the compound. 4. supersaturated with the compound.
an unsaturated solution of the compound. pure solvent.
14. Sodium iodide in anhydrous acetone reacts most rapidly with 1.
4.
CH3CH2CH2Br
2.
CH2=CHBr
(CH3)3CBr
5.
3. CH3 Br
15.
CH3CH=CHCH2OH reacts with HBr to give which two bromobutenes? 1.
CH3CH=CHCH2Br
+
CH3CH=CBrCH3
2.
CH3CH=CHCH2Br
+ CH3CHBrCH=CH2
3.
CH2=CHCH2CH2Br +
4.
CH2=CBrCH2CH3
5.
BrCH2CH=CHCH3
CH2=CHBrCH=CH2
+ CH2=CHCH2CH2Br + BrCH2CH2CH=CH2
Br
CH3 CH CH3
16. What is the possible number of stereoisomers having the structure below? OH
OH
CH3 CH CH2 CH CH3
1. 2. 3. 4. 5.
two optically active and one meso None optically active four optically active two optically active and two meso one optically active and one meso
17. The addition of Br2 to trans-2-butene giving meso-2,3-dibromobutane can be explained by a mechanism involving 1. 3. 5.
a free radical. 2. a carbocation. a cyclic bromonium ion. 4. a carbanion. simultaneous attack by to bromine atoms.
18. Which metal catalyzed reaction would release the greatest amount of heat per CH2 unit? 1.
cyclopropane + H2 →
2.
cyclobutane + H2
3.
cyclopentane + H2
→ pentane
4.
cyclohexane + H2
→ hexane
5.
cyclododecane + H2
propane
→ butane
→ dodecane
19. What is the IUPAC name for the compound shown below? CH3
CH3
CH3 CH CH C CH3
1. 2. 3. 4. 5.
2,3-dimethyl-4-pentene 1,1-dimethyl-2-isopropylethene 2,3-dimethyl-2-pentene All of the above None of the above
20. Which dimethylcyclobutane has two optically forms? 1. 2.
trans-1,2cis-1,3-
2. cis-1,2trans-1,3-
3.
1,1-
21. The C-C-N angle in acetonitrile, CH3C≡N is 1. 4.
45° 120°
2. 5.
60° 180°
3. 109.28°
22. Which is NOT characteristic of a free radical chain reaction? 1. 2. 3. 4. 5.
It produces a mole of product for a mole of free radical initiated. It gives the product derived from the most stable free radical. It may be initiated by peroxides. It may be initiated by high heat. It may be initiated by ultraviolet light.
23. A reaction at a chiral carbon of an optically pure isomer which takes place exclusively by an SN2 reaction, and in which priorities do not change, proceeds with 1. 2. 3. 4. 5.
inversion and no racemization. inversion and some racemization. inversion and complete racemization. retention of configuration and some racemization. retention of configuration and no racemization.
24. Which would yield 2-methyl-2-pentene when refluxed with zinc dust in alcohol? Br
1.
CH3
Br
2.
CH3 CH2 CH C CH3
CH3
CH3 CH2 CH CH CH3
Br
3.
CH3
4.
CH3 CH2 CH2 C CH2 Br
Br CH3 CH3 CH2 C CH CH3
Br
Br
5.
Br
Br
CH3
CH3 CH CH CH CH3
25. Which anion is the weakest base? 1. 3.
C2H5O1CH3COO1-
2. 5.
NO31OH1-
3.
CN1-
26. Which compound would be the major product when (CH3)2CHCHBrCH2CH3 is treated with alcoholic KOH?
27.
1.
(CH3)2CHCH2CHOHCH3
2.
(CH3)2CHCHOHCH2CH3
3.
(CH3)2COCH2CH2CH3
4.
(CH3)2CHCH=CH3
5.
(CH3)2C=CHCH2CH3
If tert-butyl bromide and sodium amide (NaNH2) react, the product formed is 1. 2. 3. 4. 5.
tert-butylamine. (amines are R-NH2) tert-butylammonium bromide. a mixture of butylamines. isobutylene. (2-methylpropene) none of these.
28. In the reaction below, the product would be CH3 CH CH CH3
1. 2. 3. 4. 5.
+ H2O
H3 O+
OH CH3 CH2 CH CH3
a mixture of diastereomers. opticaly active. unresolvable. a racemate. a meso compound.
29. The rate of an SN2 reaction run in a polar aprotic solvent relative to the same reaction in a polar protic solvent would be 1. 2. 3. 4. 5.
the same. slower. faster. unpredictable. unimolecular.
30. Which of the amines listed below would have the lowest boiling point? 1. 3. 5.
CH3CH2CH2NH2 (CH3)3N (CH3)2CHNH2
2. 4.
CH3CH2NHCH3 (CH3)3CNH2
31. Racemic 2,3-dibromobutane can be made by adding bromine to 1. 3.
cis-2-butene. 1,3-butadiene.
2. 4.
1-butene. trans-2-butene.
