Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 29, Problem 29.17P
Interpretation Introduction
Interpretation: The structure of leu-enkephalin, a pentapeptide with the given sequence Tyr-Gly-Gly-Phe-Leu is to be drawn.
Concept introduction: Peptide linkage is formed between the amino group of one amino acid and the carboxyl group of other amino acid with the loss of water molecule.
Amino acids are naturally occurring compounds in which the amino group is present on the
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111
Carbonyl Chem
Choosing reagants for a Wittig reaction
What would be the best choices for the missing reagents 1 and 3 in this synthesis?
1. PPh3
3
1
2
2. n-BuLi
• Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like.
Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is.
• Note: if one of your reagents needs to contain a halogen, use bromine.
Explanation
Check
Click and drag to start drawing a structure.
×
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A student proposes the transformation below in one step of an organic synthesis. There may be one or more reactants missing from the left-hand side, but there
are no products missing from the right-hand side. There may also be catalysts, small inorganic reagents, and other important reaction conditions missing from
the arrow.
• Is the student's transformation possible? If not, check the box under the drawing area.
. If the student's transformation is possible, then complete the reaction by adding any missing reactants to the left-hand side, and adding required catalysts,
inorganic reagents, or other important reaction conditions above and below the arrow.
• You do not need to balance the reaction, but be sure every important organic reactant or product is shown.
+
T
X
O
O
лет-ле
HO
OH
HO
OH
This transformation can't be done in one step.
Determine the structures of the missing organic molecules in the following reaction:
X+H₂O
H*
H+
Y
OH
OH
Note: Molecules that share the same letter have the exact same structure.
In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X and Y. You may draw the structures in any arrangement
that you like, so long as they aren't touching.
Click and drag to start drawing a structure.
X
S
Chapter 29 Solutions
Organic Chemistry
Ch. 29 - Prob. 29.1PCh. 29 - Problem 29.2
What form exists at the isoelectric...Ch. 29 - Problem 29.3
Explain why the of the group of an...Ch. 29 - Prob. 29.4PCh. 29 - Problem 29.5
What -halo carbonyl compound is...Ch. 29 - Problem 29.6
The enolate derived from diethyl...Ch. 29 - Problem 29.7
What amino acid is formed when is...Ch. 29 - Problem 29.8
What aldehyde is needed to synthesize...Ch. 29 - Problem 29.9
Draw the products of each...Ch. 29 - Prob. 29.10P
Ch. 29 - Prob. 29.11PCh. 29 - Prob. 29.12PCh. 29 - Problem 29.13
What alkene is needed to synthesize...Ch. 29 - Problem 29.14
Draw the structure of each peptide....Ch. 29 - Problem 29.15
Name each peptide using both the...Ch. 29 - Prob. 29.16PCh. 29 - Prob. 29.17PCh. 29 - Problem 29.18
Glutathione, a powerful antioxidant...Ch. 29 - Problem 29.19
Draw the structure of the...Ch. 29 - Problem 29.20
Give the amino acid sequence of an...Ch. 29 - a What products are formed when each peptide is...Ch. 29 - Prob. 29.22PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.25PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.28PCh. 29 - Draw the product formed when the following amino...Ch. 29 - With reference to the following peptide: a...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.32PCh. 29 - Histidine is classified as a basic amino acid...Ch. 29 - Tryptophan is not classified as a basic amino acid...Ch. 29 - What is the structure of each amino acid at its...Ch. 29 - What is the predominant form of each of the...Ch. 29 - 29.37 What is the predominant form of each of the...Ch. 29 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 29 - 29.39 Draw the organic products formed in each...Ch. 29 - 29.40 What alkyl halide is needed to synthesize...Ch. 29 - 29.41 Devise a synthesis of threonine from diethyl...Ch. 29 - 29.42 Devise a synthesis of each amino acid from...Ch. 29 - Prob. 29.43PCh. 29 - Prob. 29.44PCh. 29 - Prob. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.49PCh. 29 - Prob. 29.50PCh. 29 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 29 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr:
a....Ch. 29 - Prob. 29.53PCh. 29 - Prob. 29.54PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.56PCh. 29 - Prob. 29.57PCh. 29 - Prob. 29.58PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - 29.60 Draw the organic products formed in each...Ch. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.63 Besides the Boc and Fmoc protecting groups...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - 29.65 Draw the mechanism for the reaction that...Ch. 29 - 29.66 Which of the following amino acids are...Ch. 29 - 29.67 After the peptide chain of collagen has been...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.71P
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- Predict the major products of this organic reaction. If there aren't any products, because nothing will happen, check the box under the drawing area instead. No reaction. HO. O :☐ + G Na O.H Click and drag to start drawing a structure. XS xs H₂Oarrow_forwardWhat are the angles a and b in the actual molecule of which this is a Lewis structure? H H C H- a -H b H Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal groups may have slightly different sizes. a = b = 0 °arrow_forwardWhat are the angles a and b in the actual molecule of which this is a Lewis structure? :0: HCOH a Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal that might be caused by the fact that different electron groups may have slightly different sizes. a = 0 b=0° Sarrow_forward
- Determine the structures of the missing organic molecules in the following reaction: + H₂O +H OH O OH +H OH X Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structure of the missing organic molecule X. Click and drag to start drawing a structure.arrow_forwardIdentify the missing organic reactant in the following reaction: x + x O OH H* + ☑- X H+ O O Х Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H₂O) are not shown. In the drawing area below, draw the skeletal ("line") structure of the missing organic reactant X. Click and drag to start drawing a structure. Carrow_forwardCH3O OH OH O hemiacetal O acetal O neither O 0 O hemiacetal acetal neither OH hemiacetal O acetal O neither CH2 O-CH2-CH3 CH3-C-OH O hemiacetal O acetal CH3-CH2-CH2-0-c-O-CH2-CH2-CH3 O neither HO-CH2 ? 000 Ar Barrow_forward
- What would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 2 2. n-BuLi 3 Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. • Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Explanation Check Click and drag to start drawing a structure.arrow_forwardPredict the products of this organic reaction: NaBH3CN + NH2 ? H+ Click and drag to start drawing a structure. ×arrow_forwardPredict the organic products that form in the reaction below: + OH +H H+ ➤ ☑ X - Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. Garrow_forward
- Predict the organic products that form in the reaction below: OH H+ H+ + ☑ Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. ✓ marrow_forwardDetermine the structures of the missing organic molecules in the following reaction: + H₂O +H H+ Y Z ☑ ☑ Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X, Y, and Z. You may draw the structures in any arrangement that you like, so long as they aren't touching. Molecule X shows up in multiple steps, but you only have to draw its structure once. Click and drag to start drawing a structure. AP +arrow_forwardPlease help, this is all the calculations i got!!! I will rate!!!Approx mass of KMnO in vial: 3.464 4 Moss of beaker 3×~0. z Nax200: = 29.9219 Massof weacerv after remosimgain N2C2O4. Need to fill in all the missing blanks. ง ง Approx mass of KMnO4 in vials 3.464 Mass of beaker + 3x ~0-304: 29.9219 2~0.20 Miss of beaker + 2x- 29.7239 Mass of beaker + 1x~0.2g Naz (204 29-5249 Mass of beaver after removing as qa Na₂ C₂O T1 T2 T3 Final Buiet reading Initial butet reading (int)) Hass of NaOr used for Titration -reading (mL) calculation Results: 8.5ml 17mL 27.4mL Oml Om Oml T1 T2 T3 Moles of No CO Moles of KMO used LOF KM. O used Molenty of KMNO Averagem Of KMOWLarrow_forward
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