Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 20, Problem 20.47P
Explain why metal hydride reduction gives an endo alcohol as the major product in one reaction and an exo alcohol as the major product in the other reaction.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Given the major organic product(s) of each of the following reactions. If none is predicted, write "N.R."
answer]
a.
CHỊCH, CHẤT
AIC13
H
b.
0
Cl₂
HC-
NHOCH3
FeCl3
Give the major organic product(s) for each of the following reactions or sequences of reactions. Show
all relevant stereochemistry [2 ONLY].
A
-CH2COOH
1. LIAIH THF, heat
2 HO
B.
C.
CH₂Br
Br
1. NaCN, acetone
2 H₂O, heat
1. Mg ether
3 HO
Z CO₂
What is the order of increasing acidity for the following compounds? (least to most) [2 ONLY]
A.
COOH
COOH
COOH
COOH
6666
a.
IV, I, III, II
b.
III, II, I, IV
с.
II, III, I, IV
d. III, II, IV, I
slingoros
CH3
IV
woled noise biz
Chapter 20 Solutions
Organic Chemistry
Ch. 20 - Prob. 20.1PCh. 20 - Which carbonyl groups in the anticancer drug taxol...Ch. 20 - Prob. 20.3PCh. 20 - Problem 20.4 What alcohol is formed when each...Ch. 20 - Problem 20.5 What aldehyde or ketone is needed to...Ch. 20 - Prob. 20.6PCh. 20 - Problem 20.7 Draw the products formed when is...Ch. 20 - Problem 20.8 Draw the products formed (including...Ch. 20 - Prob. 20.9PCh. 20 - Problem 20.10 Draw a stepwise mechanism for the...
Ch. 20 - Prob. 20.11PCh. 20 - Problem 20.12 Draw the products formed from ...Ch. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - Prob. 20.15PCh. 20 - Problem-20.16 Review the oxidation reactions using...Ch. 20 - Problem-20.17 Write the step(s) needed to convert ...Ch. 20 - Problem-20.18 Oct-1-yne reacts rapidly with ,...Ch. 20 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Problem 20.21 Draw the product of each reaction.
...Ch. 20 - Problem 20.22 Draw the products (including...Ch. 20 - Problem 20.23 What Grignard reagent and carbonyl...Ch. 20 - Problem 20.24 Linalool (the Chapter 9 opening...Ch. 20 - Problem 20.25 What Grignard reagent and carbonyl...Ch. 20 - Prob. 20.26PCh. 20 - Draw the products formed when each compound is...Ch. 20 - Problem 20.28 What ester and Grignard reagent are...Ch. 20 - Prob. 20.29PCh. 20 - Problem 20.30 What reagent is needed to convert ...Ch. 20 - Prob. 20.31PCh. 20 - What carboxylic acid formed from each alkyl halide...Ch. 20 - Prob. 20.33PCh. 20 - Problem 20.34 Draw the product when each compound...Ch. 20 - Problem 20.35 Synthesize each compound from...Ch. 20 - Prob. 20.36PCh. 20 - 20.37 Devise a synthesis of each alcohol from...Ch. 20 - 20.38 Draw the products formed when pentanal is...Ch. 20 - 20.39 Draw the product formed when is treated...Ch. 20 - The stereochemistry of the products of reduction...Ch. 20 - Prob. 20.41PCh. 20 - 20.42 Draw the products or each reduction...Ch. 20 - Prob. 20.43PCh. 20 - 20.44 Draw all stereoisomers formed in each...Ch. 20 - Prob. 20.45PCh. 20 - 20.46 Treatment of ketone A with ethynylithium...Ch. 20 - 20.47 Explain why metal hydride reduction gives an...Ch. 20 - Prob. 20.48PCh. 20 - 20.49 Identify the lettered compounds in the...Ch. 20 - Prob. 20.50PCh. 20 - 20.51 Draw a stepwise mechanism for the following...Ch. 20 - 20.52 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.53PCh. 20 - 20.54 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.55PCh. 20 - Prob. 20.56PCh. 20 - 20.57 What ester and Grignard reagent are needed...Ch. 20 - 20.58 What organolithium reagent and carbonyl...Ch. 20 - 20.59 What epoxide and organometallic reagent are...Ch. 20 - Prob. 20.60PCh. 20 - 20.61 Propose two different methods to synthesize...Ch. 20 - 20.62 Synthesize each compound from cyclohexanol...Ch. 20 - 20.63 Convert propan-2-ol into each compound....Ch. 20 - 20.64 Convert benzene into each compound. You may...Ch. 20 - 20.65 Design a synthesis of each compound from...Ch. 20 - 20.66 Synthesize each compound from the given...Ch. 20 - Prob. 20.67PCh. 20 - Prob. 20.68PCh. 20 - 20.69 An unknown compound A (molecular formula )...Ch. 20 - 20.70 Treatment of compound C (molecular formula )...Ch. 20 - 20.71 Treatment of compound E (molecular formula )...Ch. 20 - 20.72 Reaction of butanenitrile () with methyl...Ch. 20 - 20.73 Treatment of isobutene with forms a...Ch. 20 - 20.74 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.75PCh. 20 - 20.76 Lithium tri-sec-butylborohydride, also known...Ch. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - Prob. 20.79PCh. 20 - 20.80 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.81P
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
- With this, please answer the following questions: 1.) draw the structure of the electrophilic intermediate in this reaction. 2.) what is the role of the AlCl3 in the reaction 3.) write the complete stepwise mechanism for this reaction. Show all electron flow with arrows and include all intermediate structuresarrow_forwardConsider 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.arrow_forwardRefer 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?arrow_forward
- 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 UMarrow_forwardConsider 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_forward
- Choose 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_forwardWhat 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_forward
- QUESTION: 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_forwardIf 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_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Lipids - Fatty Acids, Triglycerides, Phospholipids, Terpenes, Waxes, Eicosanoids; Author: The Organic Chemistry Tutor;https://www.youtube.com/watch?v=7dmoH5dAvpY;License: Standard YouTube License, CC-BY