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Chapter 11 Practice Chem 12A
- What compound results when 1
- butanol is treated with P/I 2
A) CH
CH
CH
CH
I
B) racemic CH 3
CH
CHICH
C) CH
CH
CH
CH
OP(OH)
D) CH
CH
CH
CH
PI
E) Primary alcohols don't react with P/I 2
- Which alcohol reacts most rapidly with the Lucas reagent?
A) benzyl alcohol B) methanol C) 2
- Which set of reagents will best convert 2,2-dimethylpropan- 1 - ol (neopentyl alcohol) to
4,4-dimethylpentan- 2 - ol?
A) 1. HCl
- Mg
3. CH
CHO
4. H
O
B) 1. HCl, ZnCl 2
- Mg
3. CH
O
4. H
O
C) 1. SOCl 2
- Mg
3. CH
CHO
4. H
O
D) 1. HCl, ZnCl 2
- Mg
3. CH
CHO
4. H
O
- Which of the following alcohols will give a positive chromic acid test?
A) tert-butanol B) cyclohexanol C) pentan- 3 - ol D) both A and B E) both B and C
- Which reagent could be used to perform the following reaction?
A) NaOCl/TEMPO B) Swern Oxidation
C) DMP (periodane) reagent D) All reagents will work
- Which of the following reagents can be used to convert cyclopentanol to cyclopentane?
A) TsCl, pyridine followed by LiAlH 4
B) Na 2 Cr 2
O
, H
SO
C) NaBH 4 followed by H 3
O
D) H
SO
, heat followed by H 2 , Pt
E) both A and D
- Which of the following compounds has carbon in the highest oxidation state?
A) CO
B) CH
C(O)CH
C) CH
CH
OH D) CH
C(OCH
CH
- Which energetic material is a nitrate ester?
A) nitroglycerin B) TNT C) RDX D) nitromethane
- Mark all the structures below that contain an inorganic ester. (More than one answer is possible.)
A) B)
C) D)
- Identify the sequence of reactions that successfully completes the following transformation.
A) 1. BH
2. H
O
/ NaOH 3. P, I 2
B) HI / hν
C) 1. HBr / hν 2. NaI, acetone
D) A and C
E) all of the above
- What is the best way to make the ether shown below using a Williamson Ether Synthesis reaction?
A) (CH
CO
BrCH 3
B) (CH
CBr
OCH
C) (CH
COH
BrCH 3
D) (CH
CBr
HOCH
Provide the structure of the major organic product in the reaction below.
Provide the structure of the major organic product in the reaction below.
PhCH 2
CH(OH)CH
SOCl 2
Provide the structure of the major organic product in the reaction below.
Provide the structure of the major organic product that results when 1
- octanol is treated with pyridinium
chlorochromate.
Provide the structure of the major organic product in the reaction below.
Draw the products formed in the Fischer esterification reaction between acetic acid (CH 3
CO
H) and
cyclohexanol.
Provide the major organic product of the following.
What is the final product of the reaction sequence shown below, making sure to include stereochemistry as appropriate.
Provide the major organic product of the following reaction.
Show the most efficient use of the Williamson ether synthesis to prepare CH 3
CH
CH
OCH(CH
Provide the major organic product of the reaction shown.
What reagents are necessary for the following conversion?
What series of synthetic steps could be used to prepare hexan- 3 - ol from propan- 1 - ol?
What series of synthetic steps could be used to prepare (CH 3
CHCHO from (CH 3
CH?
Answer Key
Testname: CH11 PRACTICE CHEM12A
1) A
2) A
3) C
4) E
5) D
6) E
7) A
8) A
9) C, D
10) D
11) D
12) B
13) A
- PhCH 2 CHClCH 3
17) CH
(CH
CHO
Answer Key
Testname: CH11 PRACTICE CHEM12A
- Hg(OAc) 2
, CH
CH
OH
- NaBH 4
or
1) BH
2) H
O
OH
- Na
4) CH
CH
I
Note: The hydration in the second option could be accomplished with H
, H
O or Hg(OAc) 2
, H
O as well.
- 1 - methylcyclopentanol; goes via the more stable 3° carbocation
34) 1) PCC
2) CH
CH
CH
MgBr
3) H
O
or
HBr or PBr 3
Mg, Et 2
O
3) CH
CH
CHO
- Br 2 , hν
NaOEt, heat
3) BH
4) H
O
OH
5) PCC
