Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 21, Problem 21.92P
Draw stepwise mechanism for the following reaction, a key step in the synthesis of
conivaptan (trade name Vaprisol), a drug used in the treatment of low sodium levels.
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Gramicidin A can adopt more than one structure; NMR spectroscopy has revealed an “end-to-end” dimer form, and x-ray crystallography has revealed an “anti-parallel double- helical” form. Briefly outline and describe an experimentalapproach/strategy to investigate WHICH configuration (“end-to-end dimer” vs “anti-paralleldouble helical”) gramicidin adopts in an actual lipid bilayer.
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CHEM2323
Problem 2-24
Tt O
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Predict the product(s) of the following acid/base reactions. Draw curved arrows to show the formation and
breaking of bonds. If the bonds needed are not drawn out, you should redraw them.
+ BF3
(a)
(b)
HI +
(c)
OH
-BF
Problem 2-25
Use curved arrows and a proton (H+) to draw the protonated form of the following Lewis bases. Before
starting, add all missing lone pairs.
(a)
(b)
:0:
(c)
N
1
CHEM2323
PS CH02
Name:
Chapter 21 Solutions
Organic Chemistry-Package(Custom)
Ch. 21 - Rank the following compounds in order of...Ch. 21 - Prob. 21.2PCh. 21 - Give the IUPAC name for each aldehyde.Ch. 21 - Prob. 21.4PCh. 21 - Give the IUPAC name for each ketone.Ch. 21 - Prob. 21.6PCh. 21 - Prob. 21.7PCh. 21 - The boiling point of is significantly higher than...Ch. 21 - Which carbonyl group in each pair absorbs at a...Ch. 21 - Problem 21.10 Draw the structure of all...
Ch. 21 - Prob. 21.11PCh. 21 - Prob. 21.12PCh. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Problem 21.15 Draw the product of each...Ch. 21 - Prob. 21.16PCh. 21 - Prob. 21.17PCh. 21 - Outline a synthesis of each Wittig reagent from...Ch. 21 - Draw the products including stereoisomers formed...Ch. 21 - Prob. 21.20PCh. 21 - Prob. 21.21PCh. 21 - Show two methods to synthesize each alkene: a...Ch. 21 - Problem 21.22 The product formed when reacts with...Ch. 21 - What 1 amine and carbonyl compound are needed to...Ch. 21 - Prob. 21.25PCh. 21 - Prob. 21.26PCh. 21 - Prob. 21.27PCh. 21 - Problem 21.28 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.29 Draw the products of each...Ch. 21 - Problem 21.30 Label each compound as an acetal, a...Ch. 21 - Problem 21.31 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.32 Draw the products of each...Ch. 21 - Problem 21.33 Safrole is a naturally occurring...Ch. 21 - Problem 21.35 How would you use a protecting group...Ch. 21 - Prob. 21.35PCh. 21 - Problem 21.37 Two naturally occurring compounds...Ch. 21 - Problem 21.38 Draw the products of each...Ch. 21 - Prob. 21.38PCh. 21 - Problem 21.40 (a) Give the IUPAC name for A and B....Ch. 21 - 21.41 Rank the following compounds in order of...Ch. 21 - Prob. 21.41PCh. 21 - Give the IUPAC name for each compound. a. d. g. b....Ch. 21 - Give the structure corresponding to each name. a....Ch. 21 - Including stereoisomers, draw the 11 aldehydes...Ch. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - What alkyl halide is needed to prepare each Wittig...Ch. 21 - 21.46 Draw the products of each reaction.
a. e....Ch. 21 - Prob. 21.49PCh. 21 - Prob. 21.50PCh. 21 - Prob. 21.51PCh. 21 - Prob. 21.52PCh. 21 - Prob. 21.53PCh. 21 - Rank the following compounds in order of...Ch. 21 - Which compound forms the higher concentration of...Ch. 21 - Prob. 21.56PCh. 21 - What Wittig reagent and carbonyl compound are...Ch. 21 - Prob. 21.58PCh. 21 - What reagents are needed to convert each compound...Ch. 21 - What reagents are needed to convert each compound...Ch. 21 - Prob. 21.61PCh. 21 - Devise a synthesis of each alkene using a Wittig...Ch. 21 - Devise a synthesis of each compound from...Ch. 21 - Prob. 21.64PCh. 21 - Prob. 21.65PCh. 21 - Prob. 21.66PCh. 21 - Prob. 21.67PCh. 21 - Prob. 21.68PCh. 21 - Prob. 21.69PCh. 21 - 21.64 Draw a stepwise mechanism for the following...Ch. 21 - 21.65 Draw a stepwise mechanism f or the following...Ch. 21 - Prob. 21.72PCh. 21 - 21.67 Draw a stepwise mechanism for each...Ch. 21 - 21.68 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.75PCh. 21 - Prob. 21.76PCh. 21 - Prob. 21.77PCh. 21 - Prob. 21.78PCh. 21 - Prob. 21.79PCh. 21 - 21.73 Although the carbonyl absorption of cyclic...Ch. 21 - 21.74 Use the and data to determine the...Ch. 21 - 21.75 A solution of acetone in ethanol in the...Ch. 21 - Compounds A and B have molecular formula ....Ch. 21 - 21.77 An unknown compound C of molecular formula ...Ch. 21 - 21.78 An unknown compound D exhibits a strong...Ch. 21 - Prob. 21.86PCh. 21 - -D-Glucose, a hemiacetal, can be converted to a...Ch. 21 - 21.81 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.89PCh. 21 - Prob. 21.90PCh. 21 - Prob. 21.91PCh. 21 - 21.86 Draw stepwise mechanism for the following...
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- CHEM2323 Problem 2-26 Tt O PS CH02 Name: Use the curved-arrow formalism to show how the electrons flow in the resonance form on the left to give the one on the right. (Draw all lone pairs first) (a) NH2 NH2 + (b) Problem 2-27 Double bonds can also act like Lewis bases, sharing their electrons with Lewis acids. Use curved arrows to show how each of the following double bonds will react with H-Cl and draw the resulting carbocation. (a) H2C=CH2 (b) (c) Problem 2-28 Identify the most electronegative element in each of the following molecules: (a) CH2FCI F Problem 2-29 (b) FCH2CH2CH2Br (c) HOCH2CH2NH2 (d) CH3OCH2Li F 0 0 Use the electronegativity table in Figure 2.3 to predict which bond in the following pairs is more polar and indicate the direction of bond polarity for each compound. (a) H3C-Cl or Cl-CI (b) H3C-H or H-CI (c) HO-CH3 or (CH3)3Si-CH3 (d) H3C-Li or Li-OHarrow_forwardDon't used hand raitingarrow_forwardDon't used hand raitingarrow_forward
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