Practice
Section A
Name___________________________________ PID_______________________
Please place name and PID on this paper , please show all mechanisms using curved arrows to show the movement of electrons between stable intermediaates and products.
M.C. questions are worth 2 points each
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
1) Which of the following amines will react with cyclopentanone to form an enamine?
| 1) |
| 2) What is the major organic product of the following reaction? | 2) |
A) I B) II C) III D) IV
| 3) Which of the following is a pyranose ring? A) | B) | 3) |
C) Both of these are pyranose rings. D) Neither of these is a pyranose ring.
4) What is the product of the following reaction? 4)
| A) I B) II C) III D) IV | |
| 5) Identify the correct sequence of substances in degree of oxidation. A) alcohol → carboxylic acid → aldehyde B) carboxylic acid → aldehyde → alcohol C) alcohol → aldehyde → carboxylic acid D) carboxylic acid → alcohol → aldehyde | 5) |
| 6) Cyclic acetals are used as protecting groups for ketones or aldehydes because they | 6) |
are inert to all of the following reagents except
A) aqueous acid. B) oxidizing reagents.
C) reducing reagents. D) aqueous base.
| 7) What product is formed when the following compound is hydrolyzed with aqueous acid? | 7) |
| A) I B) II C) III D) IV | |
8) Using 1H NMR spectroscopy, how can you tell the difference between an aldehyde and a ketone?
| 8) |
| 9) What IR absorption is characteristic of the C=O stretch in aldehydes? | 9) |
| A) 3300 cm-1 B) 3500 cm-1 C) 2950 cm-1 D) 1710 cm-1 E) 2250 cm-1 | |
| 10) What is the product of the following reaction? | 10) |
A) I B) II C) III D) IV
11) Why can’t you use acidic conditions (such as aqueous hydrochloric acid) for the addition of a Grignard reagent to a ketone?
| 11) |
12) What class of organic product results when 1-heptyne is treated with a mixture of mercuric acetate in aqueous sulfuric acid?
| 12) |
13) Reaction of ethylmagnesium bromide with which of the following compounds yields a tertiary alcohol after quenching with aqueous acid? A) n-butyllithium
| 13) |
14) Which of the following synthetic routes works best for preparing 4-octene?
| 14) |
| 15) What would you use to prepare the following ylide from the starting phosphonium salt? | 15) |
| A) Triphenylphosphine B) 1-Bromo-2-methylpropane C) Acetic acid D) Butyl lithium | |
16) What is the purpose of a silyl ether?
| 16) |
| 17) What is the major organic product of the following reaction? | 17) |
A) B) C) D)
| 18) Which of the following is the cyclic hemiacetal formed from 4-hydroxyheptanal? | 18) |
| A) I B) II C) III D) IV E) V | |
| 19) What is the cyclic hemiacetal product formed from intramolecular cyclization of the following hydroxy aldehyde? | 19) |
| A) I B) II C) III | D) IV | |
| 20) Classify the reaction below as an oxidation, a reduction, or neither. | 20) |
(CH3)2CHCH2OH → (CH3)2CHCHO
A) reduction B) oxidation C) neither
2211 Test 4 Practice
Name__________________________________PID_____________
Please ensure your Name and PID is on this exam paper.
21. Show the products and give reaction mechanisms for the following, using curved arrows to indicate the flow of electrons using a minimum of 7 words to illustrate key points and intermediates A (10 points)
H
+
O
N
H
2
B. (6 points)
2
O
M
e
C
P
P
h
3
+
22. Show how you would make the target compound on the right form the starting compound on the left. Show reagents and conditions where appropriate, and the structures of important intermediate compounds. Do not show any (arrow pushing) mechanisms!!!!
a. (9 points)
O O
4-Steps
OEtH
O
Bonus. (7 points) Mechanism of the hemiacetal!
E
t
O
O
H
H
+
Answer Key
Testname: 2211 TEST 4A SPRING 18 SECTION 1
- E
- B
- B
- A 5) C
- A
- A
- B
- D 10) C
- B
- A
- B
- E
- D
- D
- B
- C
- B
- B
6