Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 23.9, Problem 15P
Which of the following amino acid side chains can help remove a proton from the α-carbon of an
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1. For each of the reaction "railroads" below, you are either asked to give the structure(s) of the starting
material(s) or product(s), or provide reagents/conditions to accomplish the transformation, as
indicated by the boxes.
a.
NaOMe
H+
.CO,H
HO₂C
MeOH (excess)
MeOH
H3C
Br
يع
CH3
1. LiAlH4
2. H3O+
3. PBг3
H3C
1. Et-Li
2. H3O+
-CO₂Me
-CO₂Me
OH
CH3
CH3
ল
CH3
Predict the intermediate 1 and final product 2 of this organic reaction:
NaOMe
ག1, ད།་, -
+
H
You can draw 1 and 2 in any arrangement you like.
2
work up
Note: if either 1 or 2 consists of a pair of enantiomers, just draw one structure using line bonds instead of 3D (dash and wedge)
bonds at the chiral center.
Explanation
Check
Click and drag to start drawing a structure.
Х
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What is the total energy cost associated with the compound below adopting the shown conformation?
CH3
HH
DH
CH3
Chapter 23 Solutions
Organic Chemistry
Ch. 23.2 - Compare each of the mechanisms listed here with...Ch. 23.2 - Prob. 3PCh. 23.2 - Prob. 4PCh. 23.3 - a. Draw the mechanism for the following reaction...Ch. 23.5 - Prob. 7PCh. 23.5 - Propose a mechanism for the Co2+ catalyzed...Ch. 23.6 - Prob. 9PCh. 23.7 - Prob. 10PCh. 23.7 - Prob. 12PCh. 23.7 - Prob. 13P
Ch. 23.9 - Which of the following amino acid side chains can...Ch. 23.9 - Which of the following C-terminal peptide bonds is...Ch. 23.9 - Carboxypeptidase A has esterase activity as well...Ch. 23.9 - Arginine and lysine side chains fit into trypsins...Ch. 23.9 - Explain why serine proteases do not catalyze...Ch. 23.10 - If H2 18O is used in the hydrolysis reaction...Ch. 23.10 - When apples that have been cut are exposed to...Ch. 23.11 - Prob. 22PCh. 23.11 - The pHactivity profile for glucose-6-phosphate...Ch. 23.11 - Draw the pH-activity profile for an enzyme that...Ch. 23.12 - Prob. 25PCh. 23.12 - Draw the mechanism for the hydroxide ion-catalyzed...Ch. 23.12 - What advantage does the enzyme gain by forming an...Ch. 23.12 - Prob. 28PCh. 23.12 - Aldolase shows no activity if it is incubated with...Ch. 23 - Which of the following parameters would be...Ch. 23 - Prob. 30PCh. 23 - Prob. 31PCh. 23 - Prob. 32PCh. 23 - Indicate the type of catalysis that is occurring...Ch. 23 - The deuterium kinetic isotope effect (KH2O/KD2O)...Ch. 23 - Prob. 35PCh. 23 - Co2+ catalyzes the hydrolysis of the lactam shown...Ch. 23 - there are two kinds of aldolases. Class I...Ch. 23 - Prob. 38PCh. 23 - The hydrolysis of the ester shown here is...Ch. 23 - Prob. 40PCh. 23 - At pH = 12, the rate of hydrolysis of ester A is...Ch. 23 - 2-Acetoxycyclohexyl tosylate reacts with acetate...Ch. 23 - Proof that an imine was formed between aldolase...Ch. 23 - Prob. 44PCh. 23 - a. Explain why the alkyl halide shown here reacts...Ch. 23 - Triosephosphate isomerase (TIM) catalyzes the...
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- ΗΝ, Draw Final Product C cyclohexanone pH 4-5 Edit Enamine H3O+ CH3CH2Br THF, reflux H Edit Iminium Ionarrow_forwardHow many hydrogen atoms are connected to the indicated carbon atom?arrow_forwardIdentify the compound with the longest carbon - nitrogen bond. O CH3CH2CH=NH O CH3CH2NH2 CH3CH2C=N CH3CH=NCH 3 The length of all the carbon-nitrogen bonds are the samearrow_forward
- Identify any polar covalent bonds in epichlorohydrin with S+ and 8- symbols in the appropriate locations. Choose the correct answer below. Η H's+ 6Η Η Η Η Η Ηδ Η Ο Ο HH +Η Η +Η Η Η -8+ CIarrow_forwardH H:O::::H H H HH H::O:D:D:H HH HH H:O:D:D:H .. HH H:O:D:D:H H H Select the correct Lewis dot structure for the following compound: CH3CH2OHarrow_forwardRank the following compounds in order of decreasing boiling point. ннннн -С-С-Н . н-с- ННННН H ΗΤΗ НННН TTTĪ н-с-с-с-с-о-н НННН НН C' Н н-с-с-с-с-н НН || Ш НННН H-C-C-C-C-N-H ННННН IVarrow_forward
- Rank the following compounds in order of decreasing dipole moment. |>||>||| ||>|||>| |>|||>|| |||>||>| O ||>>||| H F H F H c=c || H c=c F F IIIarrow_forwardchoose the description that best describes the geometry for the following charged species ch3-arrow_forwardWhy isn't the ketone in this compound converted to an acetal or hemiacetal by the alcohol and acid?arrow_forward
- What is the approximate bond angle around the nitrogen atom? HNH H Harrow_forwardOH 1. NaOCH2CH3 Q 2. CH3CH2Br (1 equiv) H3O+ Select to Draw 1. NaOCH2 CH3 2. CH3Br (1 equiv) heat Select to Edit Select to Drawarrow_forwardComplete and balance the following half-reaction in acidic solution. Be sure to include the proper phases for all species within the reaction. S₂O₃²⁻(aq) → S₄O₆²⁻(aq)arrow_forward
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