Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 22.SE, Problem 59AP
Interpretation Introduction
Interpretation:
Among cis- and trans-tert-butyl-2-methylcyclohexanones, which isomer is more stable is to be stated and explained.
Concept introduction:
Two substituents with 1,3-cis relationship in cyclohexenones will have a diequatorial orientation while two substituents with 1,3-trans relationship in cyclohexenones will have an axial-equatorial orientation. In substituted cyclohexenones the conformation which contain bulky substituents at equatorial position are more stable.
To state and explain:
Among cis- and trans-tert-butyl-2-methylcyclohexanones, which isomer is more stable?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
G.133.
Pyrethrin II and pyrethrosin are two natural products isolated from plants of the chrysanthemum family. Pyrethrin II is a natural insecticide and is marketed as such.
Q,)State the number of stereoisomers possible for each molecule.
Br2 in CCl4
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
Knowledge Booster
Similar questions
- Ethylene oxide reacts readily with HO- because of the strain in the three-membered ring. Explain why cyclopropane, a compound with approximately the same amount of strain, does not react with HO-.arrow_forwardDraw the structure of (S,S)-ethambutol, a drug used to treat tuberculosis that is 10 times more potent than any of its other stereoisomers.arrow_forward4-Chloro-2-pentene has a double bond that can have either the E or the Z configuration and a stereogenic center that can have either the R or the S configuration. How many stereoisomers arepossible altogether? Draw the structure of each, and group the pairs of enantiomers.arrow_forward
- G.45.arrow_forward5) Use compounds X, Y and Z (shown below) to answer the following questions. H. H3C" "CH3 ОН CH3 compound X compound Y compound Z a) Is compound X classified as cis, trans or neither? b) Is compound Y classified as E, Z or neither? c) Is compound Z classified as R, S or neither? d) Are compounds X and Y constitutional isomers of each other? (YES or NO) e) Are compounds Y and Z constitutional isomers of each other? (YES or NO) f) Classify compound Y as a primary, secondary or tertiary alcohol. g) Which compound(s) is(are) chiral? h) Give the IUPAC name for compound Z, omitting the absolute configuration (R or S) designation. i) In the indicated spaces below, draw stereoisomers of compounds X, Y and Z. stereoisomer of compound X stereoisomer of compound Y stereoisomer of compound Zarrow_forwardDraw the organic product of the following reaction. CH3 m-CICgH,CO;H • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If the reaction produces a racemic mixture, just draw one stereoisomer. • If more than one product is possible, only draw the major product. opy astearrow_forward
- Compound 1 Br Bri НІ T ... H The correct IUPAC names are: Compound 2 H Br Br I.. H Br The compounds are diastereomers not isomeric enantiomers identical constitutional isomers Compound 1: (2R, 3R)-1,2,3-tribromobutane, Compound 2: (2S, 3R)-1,2,3-tribromobutane Compound 1: (2R, 3S)-1,2,3-tribromobutane, O Compound 1: (2R,3R)-1,2,3-tribromobutane, Compound 2: (2S,3S)-1,2,3-tribromobutane Compound 2: (2R, 3R)-1,2,3-tribromobutane O Compound 1: (2S,3S)-1,2,3-tribromobutane, Compound 2: (2R,3S)-1,2,3-tribromobutanearrow_forwardOF OFFICI NSGR my Which of the following aldehydes would be the most soluble in water? (Hint: Remember the relation between the number of carbons in aldehydes and ketones and their solubility in water.) O CH3–CH2–CH2–CH2–CHO O CH3-CH2–CH2–CH2–CH2–CHO O CH3-CH2–CH2–CH2–CH2–CH2–CHO O CH3–CH2–CH2–CHO H f5 % 5 (O & hip 4+ CO fgarrow_forwardDraw the structure of (S,S)-ethambutol, a drug used to treat tuberculosis that is 10 times more potent than any of its other stereoisomers.arrow_forward
- Draw the alkene that would react with the reagent given to account for the product formed. ? + + H₂O **** H₂S04 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. CH3 CH3 CHCCH3 | | OH CH3 +1arrow_forwardNeed help, please.arrow_forwardOn a cyclohexane ring, an axial carboxyl group has a conformational energy of 5.9 kJ (1.4 kcal)/mol relative to an equatorial carboxyl group. Consider the equilibrium for the alternative chair conformations of trans-1,4-cyclohexanedicarboxylic acid. Draw the less stable chair conformation on the left of the equilibrium arrows and the more stable chair on the right. Calculate DG0 for the equilibrium as written and calculate the ratio of the more stable chair to the less stable chair at 25°C.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
