Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 18, Problem 18.41SP
Acetals can serve as protecting groups for 1,2-
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Consider the data below to answer the following questions.
Cyanohydrins are important intermediates in the synthesis of a-hydroxycarboxylic acids from ketones
and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic
acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a
cyanohydrin is treated with aqueous base the original carbonyl compound is isolated.
HO
H
HCEN
H-3-
HO'
NaOH
HO
cyanohychin
a.
a nucleophilic substitution
b.
an electrophilic addition
C10
OH
CH-COOH
A. The reaction of an aldehyde with hydrogen cyanide is an example of
+ NaCN + H₂O
reaction.
H-
C.
an electrophilic substitution
d. a nucleophilic addition
B. Identify the electrophile in the reaction of benzaldehyde with hydrogen cyanide.
Refer to the data below to answer the following questions:
The octapeptide saralasin is a specific antagonist of angiotensin II. A derivative of saralasin is used
therapeutically as an antihypertensive. Amino acid analysis of saralasin show the presence of the following
amino acids:
Ala, Arg, His, Pro, Sar, Tyr, Val, Val
A. Sar is the abbreviation for sarcosine, N-methyl aminoethanoic acid. Draw the structure of sarcosine.
B. N-Terminal analysis by the Edman method shows saralasin contains sarcosine at the N-terminus.
Partial hydrolysis of saralasin with dilute hydrochloric acid yields the following fragments:
Tyr-Val-His
Sar-Arg-Val
His-Pro-Ala
Val-Tyr-Val
Arg-Val-Tyr
What is the structure of saralasin?
Give the major organic product(s) of each of the following reactions or sequences of reactions. Show
all relevant stereochemistry.[4 only]
CH3
A.
B.
HNO
H₂Pt
H₂SO4 hano
NaN
1. LIAH ether
Br
4
2 H₂O
C.
D.
E.
CH3CH2-CH2CH3 + HCl
Br
NH₂
CH3
ON
CH-CH3
Br HNOZ CUCI
11,504
HC)
1. HNO H SO
NH₂
2
UM
Chapter 18 Solutions
Organic Chemistry (9th Edition)
Ch. 18.3 - Give the IUPAC name and (if possible) a common...Ch. 18.5D - NMR spectra for two compounds are given here,...Ch. 18.5D - Why were no products from the McLafferty...Ch. 18.5D - Use equations to show the fragmentation leading to...Ch. 18.5E - Prob. 18.5PCh. 18.7D - Show how you would synthesize each compound from...Ch. 18.8 - Prob. 18.7PCh. 18.9 - Predict the products of the following reactions....Ch. 18.9 - Show how the following transformations may be...Ch. 18.10 - Prob. 18.10P
Ch. 18.11 - Show how you would accomplish the following...Ch. 18.11 - Prob. 18.12PCh. 18.12 - Propose mechanisms for a. the acid-catalyzed...Ch. 18.12 - Rank the following compounds in order of...Ch. 18.13 - Prob. 18.15PCh. 18.13 - Show how you would accomplish the following...Ch. 18.14 - Prob. 18.17PCh. 18.14 - Prob. 18.18PCh. 18.14 - Prob. 18.19PCh. 18.14 - Prob. 18.20PCh. 18.15 - 2,4-Dinitrophenylhydrazine is frequently used for...Ch. 18.15 - Prob. 18.22PCh. 18.15 - Prob. 18.23PCh. 18.16 - Prob. 18.24PCh. 18.16 - Prob. 18.25PCh. 18.16 - Show what alcohols and carbonyl compounds give the...Ch. 18.16 - In the mechanism for acetal hydrolysis shown, the...Ch. 18.16 - Prob. 18.28PCh. 18.17 - Show how you would accomplish the following...Ch. 18.18 - Prob. 18.30PCh. 18.18 - Prob. 18.31PCh. 18.18 - Prob. 18.32PCh. 18.18 - Show how Wittig reactions might be used to...Ch. 18.19 - Predict the major products of the following...Ch. 18.20C - Prob. 18.35PCh. 18.20C - Predict the major products of the following...Ch. 18 - Draw structures of the following derivatives. a....Ch. 18 - Prob. 18.38SPCh. 18 - Predict the major products of the following...Ch. 18 - Rank the following carbonyl compounds in order of...Ch. 18 - Acetals can serve as protecting groups for...Ch. 18 - Sketch the expected proton NMR spectrum of...Ch. 18 - A compound of formula C6H10O2 shows only two...Ch. 18 - The proton NMR spectrum of a compound of formula...Ch. 18 - The following compounds undergo McLafferty...Ch. 18 - An unknown compound gives a molecular ion of m/z...Ch. 18 - Show how you would accomplish the following...Ch. 18 - Prob. 18.48SPCh. 18 - Prob. 18.49SPCh. 18 - Propose mechanisms for the following reactions.Ch. 18 - Show how you would accomplish the following...Ch. 18 - Show how you would synthesize the following...Ch. 18 - Predict the products formed when cyclohexanone...Ch. 18 - Predict the products formed when...Ch. 18 - Show how you would synthesize octan-2-one from...Ch. 18 - Prob. 18.56SPCh. 18 - Both NaBH4 and NaBD4 are commercially available,...Ch. 18 - When LiAIH4 reduces 3-methylcyclopentanone, the...Ch. 18 - Prob. 18.59SPCh. 18 - Show how you would accomplish the following...Ch. 18 - There are three dioxane isomers 1,2-dioxane,...Ch. 18 - Two structures for the sugar glucose are shown on...Ch. 18 - Prob. 18.63SPCh. 18 - Prob. 18.64SPCh. 18 - Prob. 18.65SPCh. 18 - Prob. 18.66SPCh. 18 - Within each set of structures, indicate which will...Ch. 18 - Prob. 18.68SPCh. 18 - Prob. 18.69SPCh. 18 - Prob. 18.70SPCh. 18 - The UV spectrum of an unknown compound shows...Ch. 18 - a. Simple aminoacetals hydrolyze quickly and...Ch. 18 - The mass spectrum of unknown compound A shows a...Ch. 18 - Prob. 18.74SPCh. 18 - Prob. 18.75SPCh. 18 - Prob. 18.76SPCh. 18 - Prob. 18.77SP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Consider the Grignard reaction below to answer the following questions. A Mgar 1. ether + MyC CH3 2H3O C B a. The electrophile in this reaction is: b. The nucleophile in this reaction is: c. The alcohol product can be classified as a: a. 1° alcohol b. 2° alcohol C. 3° alcohol d. 4° alcohol HO CH3 CHarrow_forwardGive the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry A. CH₂OH PCC CH2Cl2 HOO B. H KCN HCN of b C. 1. CH,MgBr, ether 2 HO* D. Choose the BEST reagent for carrying out each of the following conversions. CO₂CH3 CO₂CH3 OH CO₂H сон ن نے a. LiAlH4, ether at abinayo iss c b. NaBH4, ethanol C. CrO3, pyridine d. H₂/Pd d notsiolarrow_forwardChoose the best reagent for carrying out the following reactions from the list below. Place the letter of the reagent(s) in the box over the reaction arrow. Use only one letter per box. OH OH CH CH CH3 CHS CH3 f OH OCH 3 H A. NaH, then CHI B. C. m-ClC6H4COзH D. E. warm H2SO4/H₂O F. G. H₂/Pd H. I. Cl₂, H₂O J. NaOCH3, CH3OH CH3MgBr in ether, then H3O+ Hg(O2CCF3)2, CH3OH PCC, CH2Cl2 LiAlH4 in ether, then H3O+arrow_forward
- What is the product of the reaction of 2,4-pentanedione with phenylhydrazine?arrow_forwardIn the reaction of naphthalene with CrO3 in acetic acid. Indicate whether a different product is obtained if carried out at 25°C or with heating (A).arrow_forwardQUESTION: Fill in the answers in the empty green boxes 1. Step 2 2. Step 3 3. Step 4 (SUM) 4. Step 5 (df) (GIVEN) 5. Determine S y/x value *The data values have been provided in the worksheet attached in the first image*arrow_forward
- If the symbol A is placed in a reaction, at what temperature does it take place?arrow_forwardBy malonic or acetylacetic synthesis, synthesize 3-methyl-4-oxopentanoic acid (indicate the formulas of the compounds).arrow_forwardoalmitic acid is a 16 carbon acid. In a balanced equation, the products of the sponification of tripalmitin (glyceryl tripalmitate are blank.arrow_forward
- Write the esterification reaction mechanism of salicylic acid and acetic acid to produce aspirin (acetylsalicylic acid). Note: salicylic acid will act as the alcoholarrow_forwardWhat type of interaction would you expect between the following R groups in the tertiary structure of a protein? O -CH2-CO and -CH2-CH2-CH2-CH2-NH3+ a. disulfide bonds b. salt bridges c. hydrogen bonds HO abios vist anisinoo tedt bigil s ai loistaslor sale! 10 OUT d. hydrophobic interactions e. peptide bondsarrow_forward4. True or false: This skeletal structure represents a saturated fatty acid. Ini to 0 fale) me OH faistong starrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY